JP6950872B2 - Ketone or oxime compounds, and herbicides - Google Patents

Description

The present invention relates to novel ketones or oxime compounds or salts thereof, and pesticides containing ketones or oxime compounds or salts thereof as active ingredients, particularly herbicides. Further, the pesticide in the present invention means an insecticide / acaricide, a nematode, a herbicide, a fungicide, etc. in the field of agriculture and horticulture.

For example, Patent Documents 1 and 2 disclose certain ketones or oxime compounds, but do not disclose any ketones or oxime compounds according to the present invention.

International Publication No. 2001/017792 International Publication No. 2003/062244 International Publication No. 2010/000773 International Publication No. 2010/069834

An object of the present invention is a highly safe active ingredient of a herbicide, which is surely effective against various weeds with a lower drug amount and alleviates problems such as soil contamination and effects on post-crops. Is to provide useful chemicals.

As a result of intensive research aimed at solving the above problems, the present inventors have found that a novel ketone or oxime compound represented by the following formula (1) according to the present invention has excellent herbicidal activity as a herbicide and a target. The present invention has been completed by finding that it is an extremely useful compound having high safety for the crops and having almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

That is, the present invention relates to the following [1] to [151].

［式中、Ｂは、Ｂ−１、Ｂ−２又はＢ−３のいずれかで示される環を表し、

Ｑは、酸素原子、硫黄原子又はＮＯＲ^７を表し、
Ａは、水素原子、Ｃ_１〜Ｃ_６アルキル、Ｒ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、−Ｓ（Ｏ）_ｒ２Ｒ^１、−Ｃ（Ｏ）ＯＲ^１、−Ｃ（Ｓ）ＯＲ^１、−Ｃ（Ｏ）ＳＲ^１、−Ｃ（Ｓ）ＳＲ^１、−Ｃ（Ｏ）Ｒ^２、−Ｃ（Ｓ）Ｒ^２、−Ｃ（Ｏ）Ｎ（Ｒ^４）Ｒ^３、−Ｃ（Ｓ）Ｎ（Ｒ^４）Ｒ^３、−Ｓ（Ｏ）_２Ｎ（Ｒ^４）Ｒ^３、−Ｐ（Ｏ）（ＯＲ^１）_２又は−Ｐ（Ｓ）（ＯＲ^１）_２を表し、
Ｒ^１は、Ｃ_１〜Ｃ_８アルキル、Ｒ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、フェニル又は（Ｚ^２）_ｑ２で置換されたフェニルを表し、
Ｒ^２は、水素原子、Ｃ_１〜Ｃ_８アルキル、Ｒ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、−Ｃ（＝ＮＯＲ^３１）Ｒ^３２、フェニル、（Ｚ^２）_ｑ２で置換されたフェニル、ナフチル、（Ｚ^２）_ｑ２で置換されたナフチル、Ｄ１−１〜Ｄ１−４２、Ｄ１−８１又はＤ１−８４を表し
Ｒ^３及びＲ^４は、各々独立して水素原子、Ｃ_１〜Ｃ_６アルキル、Ｒ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、フェニル、（Ｚ^２）_ｑ２で置換されたフェニル、Ｄ１−３２、Ｄ１−３３又はＤ１−３４を表すか、或いは、Ｒ^３はＲ^４と一緒になってＣ_２〜Ｃ_７のアルキレン鎖又はＣ_２〜Ｃ_７のアルケニレン鎖を形成することにより、Ｒ^３及びＲ^４が結合する窒素原子と共に３〜８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ_１〜Ｃ_６アルキル、オキソ又はチオキソによって任意に置換されてもよく、
Ｒ^５は、ハロゲン原子、シアノ、ニトロ、Ｃ_３〜Ｃ_８シクロアルキル、−ＯＲ^３１、−Ｓ（Ｏ）_ｒ２Ｒ^３１、−Ｃ（Ｏ）ＯＲ^３１、−Ｃ（Ｏ）Ｒ^３２、−Ｎ（Ｒ^３４）Ｒ^３３、−Ｓｉ（Ｒ^３２ａ）（Ｒ^３２ｂ）Ｒ^３２ｃ、フェニル、（Ｚ^２）_ｑ２で置換されたフェニル、Ｄ１−１、Ｄ１−３２、Ｄ１−３３又はＤ１−３４を表すか、或いは、２つのＲ^５が同一の炭素上に置換している場合、２つのＲ^５は一緒になってオキソ、チオキソ、イミノ
、Ｃ_１〜Ｃ_６アルキルイミノ、Ｃ_１〜Ｃ_６アルコキシイミノ又はＣ_１〜Ｃ_６アルキリデンを形成してもよく、
Ｒ^６は、水素原子、Ｃ_１〜Ｃ_６アルキル、Ｒ^１５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^１５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^１５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^１５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^１５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、−Ｃ（＝ＮＯＲ^１６）Ｒ^１７、フェニル、（Ｚ^１）_ｑ１で置換されたフェニル、Ｄ１−３２、Ｄ１−３３、Ｄ１−３４、Ｄ１−３６、Ｄ１−３７又はＤ１−３８を表し、
Ｒ^７は、水素原子、Ｃ_１〜Ｃ_８アルキル、Ｒ^１５ｂで任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^１５ｂで任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^１５ｂで任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^１５ｂで任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^１５ｂで任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、フェニル又は（Ｚ^１）_ｑ１で置換されたフェニルを表し、
Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ及びＲ^９ｂは、各々独立して水素原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、−ＯＲ^１６ａ、−Ｓ（Ｏ）_ｒ１Ｒ^１６ａ、−Ｃ（Ｏ）ＯＲ^１６ａ、−Ｃ（Ｏ）Ｒ^１７ａ、−Ｃ（Ｏ）Ｎ（Ｒ^１９ａ）Ｒ^１８ａ、−Ｃ（＝ＮＯＲ^１６ａ）Ｒ^１７ａ、フェニル又は（Ｚ^１）_ｑ１で置換されたフェニルを表し、
Ｒ^１０、Ｒ^１１及びＲ^１２は、各々独立して水素原子又はＣ_１〜Ｃ_６アルキルを表し、
Ｒ^１５は、ハロゲン原子、シアノ、Ｃ_３〜Ｃ_８シクロアルキル、−ＯＲ^１６、−Ｓ（Ｏ）_ｒ１Ｒ^１６、フェニル、（Ｚ^１）_ｑ１で置換されたフェニル、Ｄ１−７、Ｄ１−１１、Ｄ１−２２、Ｄ１−３２、Ｄ１−３３又はＤ１−３４を表し、
Ｒ^１５ｂは、ハロゲン原子、シアノ、Ｃ_３〜Ｃ_８シクロアルキル、ハロ（Ｃ_３〜Ｃ_８）シクロアルキル、−ＯＲ^１６ｂ、−Ｓ（Ｏ）_ｒ１Ｒ^１６ｂ、−Ｃ（Ｏ）ＯＲ^１６ｂ、−Ｃ（Ｏ）Ｎ（Ｒ^１８ｂ）Ｒ^１９ｂ、−Ｃ（＝ＮＯＲ^１６ｂ）Ｒ^１７ｂ、−Ｎ（Ｒ^１８ｂ）Ｒ^１９ｂ、−Ｓｉ（Ｒ^３２ａ）（Ｒ^３２ｂ）Ｒ^３２ｃ、フェニル、（Ｚ^１）_ｑ１で置換されたフェニル、Ｄ１−３２、Ｄ１−３３、Ｄ１−３４、Ｄ１−３６、Ｄ１−３７、Ｄ１−３８、Ｄ１−８１又はＤ１−８４を表すか、或いは、２つのＲ^１５ｂが同一の炭素上に置換している場合、２つのＲ^１５ｂは一緒になってオキソ、チオキソ、イミノ、Ｃ_１〜Ｃ_６アルキルイミノ、Ｃ_１〜Ｃ_６アルコキシイミノ又はＣ_１〜Ｃ_６アルキリデンを形成してもよく、
Ｒ^１６、Ｒ^１６ａ、Ｒ^１６ｂ、Ｒ^１７、Ｒ^１７ａ、Ｒ^１７ｂ、Ｒ^１８ａ及びＲ^１９ａは、各々独立して水素原子又はＣ_１〜Ｃ_６アルキルを表し、
Ｒ^１８ｂ及びＲ^１９ｂは、各々独立して水素原子、Ｃ_１〜Ｃ_６アルキル又はＲ^２０で任意に置換された（Ｃ_１〜Ｃ_６）アルキルを表すか、或いは、Ｒ^１８ｂはＲ^１９ｂと一緒になってＣ_２〜Ｃ_７のアルキレン鎖又はＣ_２〜Ｃ_７のアルケレン鎖を形成することにより、Ｒ^１８ｂ及びＲ^１９ｂが結合する窒素原子と共に３〜８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つオキソ又はチオキソによって任意に置換されてもよく、
Ｒ^２０は、フェニル又は（Ｚ^１）_ｑ１で置換されたフェニルを表し、
Ｄ１−１乃至Ｄ１−４２、Ｄ１−８１、Ｄ１−８４は、各々下記の構造で表される環を表し、

Ｘ^１は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル又はＣ_３〜Ｃ_８シクロアルキルを表し、ｇ２、ｇ３又はｇ４が２以上の整数を表すとき、各々のＸ^１は互いに同一であっても又は互いに相異なってもよく、更に２つのＸ^１が隣接する場合には、隣接する２つのＸ^１は、−ＣＨ＝ＣＨＣＨ＝ＣＨ−を形成することにより、それぞれのＸ^１が結合する炭素原子と共に６員環を形成してもよく、このとき環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル又はＣ_１〜Ｃ_６アルキルスルホニルによって任意に置換されてもよく、
Ｘ^１ａは、水素原子又はＣ_１〜Ｃ_６アルキルを表し、
Ｘ^１ｂは、Ｃ_１〜Ｃ_６アルキルを表し、
Ｚは、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、Ｒ^４５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^４５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^４５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_３〜Ｃ_８シクロアルケニル、Ｒ^４５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^４５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、−ＯＲ^４１、−Ｓ（Ｏ）_ｒ３Ｒ^４１、−Ｃ（Ｏ）ＯＲ^４１、−Ｃ（Ｏ）Ｒ^４２、−Ｃ（＝ＮＯＲ^４１）Ｒ^４２、−Ｎ（Ｒ^４４）Ｒ^４３、フェニル、（Ｚ^３）_ｑ３で置換されたフェニル、Ｄ１−１、Ｄ１−２、Ｄ１−７、Ｄ１−１０、Ｄ１−１１、Ｄ１−２２、Ｄ１−３２、Ｄ１−３３、Ｄ１−３４、Ｄ１−３６、Ｄ１−３７又はＤ１−３８を表し、ｑが２以上の整数を表すとき、各々のＺは互いに同一であっても又は互いに相異なってもよく、
Ｚ^１は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ又はＣ_１〜Ｃ_６アルコキシカルボニルを表し、ｑ１が２以上の整数を表すとき、各々のＺ^１は互いに同一であっても又は互いに相異なってもよく、
Ｚ^２は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、−ＯＲ^５１、−Ｓ（Ｏ）_ｒ２Ｒ^５１、−Ｃ（Ｏ）ＯＲ^５１ａ、−Ｃ（Ｏ）Ｒ^５２、−Ｃ（Ｏ）Ｎ（Ｒ^５４）Ｒ^５３、−Ｃ（Ｓ）Ｎ（Ｒ^５４）Ｒ^５３又は−Ｎ（Ｒ^５４）Ｒ^５３を表し、ｑ２が２以上の整数を表すとき、各々のＺ^２は互いに同一であっても又は互いに相異なってもよく、更に、２つのＺ^２が隣接する場合には、隣接する２つのＺ^２は−Ｎ＝ＣＨＣＨ＝ＣＨ−，−ＣＨ＝ＮＣＨ＝ＣＨ−，−Ｎ＝ＮＣＨ＝ＣＨ−，−ＣＨ＝ＮＮ＝ＣＨ−，−Ｎ＝ＣＨＣＨ＝Ｎ−又は−Ｎ＝ＣＨＮ＝ＣＨ−を形成することにより、それぞれのＺ^２が結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル又はＣ_１〜Ｃ_６アルキルスルホニルによって任意に置換されてもよく、
Ｚ^３は、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル又はＣ_１〜Ｃ_６アルキルスルホニルを表し、ｑ３が２以上の整数を表すとき、各々のＺ^３は互いに同一であっても又は互いに相異なってもよく、
Ｒ^３１は、水素原子、Ｃ_１〜Ｃ_６アルキル、Ｒ^３５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、−Ｃ（Ｏ）Ｒ^３７、フェニル、（Ｚ^２）_ｑ２で置換されたフェニル、ナフチル又は（Ｚ^２）_ｑ２で置換されたナフチルを表し、
Ｒ^３２は、水素原子、Ｃ_１〜Ｃ_６アルキル又はＲ^３５で任意に置換された（Ｃ_１〜Ｃ_６）アルキルを表し、
Ｒ^３２ａ、Ｒ^３２ｂ及びＲ^３２ｃは、各々独立してＣ_１〜Ｃ_６アルキルを表し、
Ｒ^３３及びＲ^３４は、各々独立して水素原子、Ｃ_１〜Ｃ_６アルキル、−Ｃ（Ｏ）ＯＲ^３６又は−Ｃ（Ｏ）Ｒ^３７を表し、
Ｒ^３５は、ハロゲン原子、Ｃ_１〜Ｃ_６アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル、Ｃ_１〜Ｃ_６アルキルスルホニル又はフェニルを表し、
Ｒ^３６は、Ｃ_１〜Ｃ_６アルキルを表し、
Ｒ^３７は、水素原子、Ｃ_１〜Ｃ_６アルキル、フェニル又は（Ｚ^２）_ｑ２で置換されたフェニルを表し、
Ｒ^４１は、水素原子、Ｃ_１〜Ｃ_６アルキル、Ｒ^４５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、フェニル、（Ｚ^３）_ｑ３で置換されたフェニル、Ｄ１−３２、Ｄ１−３３又はＤ１−３４を表し、
Ｒ^４２は、水素原子又はＣ_１〜Ｃ_６アルキルを表し、
Ｒ^４３及びＲ^４４は、各々独立して水素原子、Ｃ_１〜Ｃ_６アルキル、Ｃ_１〜Ｃ_６アルコキシカルボニル又はＣ_１〜Ｃ_６アルキルカルボニルを表し、
Ｒ^４５は、ハロゲン原子、Ｃ_３〜Ｃ_８シクロアルキル、−ＯＨ、Ｃ_１〜Ｃ_６アルコキシ、Ｃ_１〜Ｃ_１０アルコキシカルボニル、−Ｓｉ（Ｒ^３２ａ）（Ｒ^３２ｂ）Ｒ^３２ｃ、フェニル、（Ｚ^３）_ｑ３で置換されたフェニル、Ｄ１−３２、Ｄ１−３３又はＤ１−３４を表すか、或いは、２つのＲ^４５が同一の炭素上に置換している場合、２つのＲ^４５は一緒になってオキソ、チオキソ、イミノ、Ｃ_１〜Ｃ_６アルキルイミノ、Ｃ_１〜Ｃ_６アルコキシイミノ又はＣ_１〜Ｃ_６アルキリデンを形成してもよく、
Ｒ^５１は、水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、フェニル、ハロゲン原子によって任意に置換されたフェニル又はＤ１−３９を表し、
Ｒ^５１ａ及びＲ^５２は、各々独立して水素原子又はＣ_１〜Ｃ_６アルキルを表し、
Ｒ^５３及びＲ^５４は、各々独立して水素原子、Ｃ_１〜Ｃ_６アルキル又はＣ_１〜Ｃ_６アルキルカルボニルを表し、
ｆ５は、０、１、２、３、４又は５の整数を表し、
ｆ７は、０、１、２、３、４、５、６又は７の整数を表し、
ｇ１及びｐは、各々独立して０又は１の整数を表し、
ｇ２、ｍ、ｎ、ｒ１、ｒ２及びｒ３は、各々独立して０、１又は２の整数を表し、
ｇ３は、０、１、２又は３の整数を表し、
ｇ４は、０、１、２、３又は４の整数を表し、
ｑ、ｑ１、ｑ２及びｑ３は、各々独立して１、２、３、４又は５の整数を表す。〕で表されるケトン若しくはオキシム化合物又はそれらの塩。 [1]
Equation (1):

[In the formula, B represents the ring represented by either B-1, B-2 or B-3.

Q represents an oxygen atom, a sulfur atom or NOR ⁷ .
A was optionally substituted with a hydrogen atom, C _{1 to} C ₆ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, R ⁵ (C ₃ to C 3 to C 6). C ₈ ) Cycloalkyl, C _{2 to} C ₆ alkenyl, C _{3 to} C ₈ cycloalkenyl, optionally substituted with ^{R 5} _{(C 3 to} C ₈ ) cycloalkenyl, optionally substituted with ^{R 5} _{(C 2)} -C _{6) alkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) ^{alkynyl, -S (O) r2 R 1}} , -C (O) OR 1, -C ( S) OR ¹ , -C (O) SR ¹ , -C (S) SR ¹ , -C (O) R ² , -C (S) R ² , -C (O) N (R ⁴ ) R ³ , Represents -C (S) N (R ⁴ ) R ³ , -S (O) ₂ N (R ⁴ ) R ³ , -P (O) (OR ¹ ) ₂ or -P (S) (OR ¹ ) ₂ . ,
R ¹ was optionally substituted with _{C 1 to} C ₈ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, optionally substituted with ^{R 5} _{(C 3 to} C _8). ) _cycloalkyl, C 2 -C ₆ alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C ₈ ) represents _{cycloalkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ alkynyl, phenyl substituted with phenyl or ^(Z _{2) q2,}
R ² is optionally substituted with a hydrogen atom, C _{1 to} C ₈ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, R ⁵ (C _3). ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ alkenyl, optionally substituted with ^{R 5} _{(C 2} ~ C ₆ ) alkenyl, C ₃ ~ C ₈ cycloalkenyl, optionally substituted with ^{R 5} _{(C 3)} -C _{8) cycloalkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ ^{alkynyl, -C (= NOR 31) R} 32, ^phenyl, substituted with (Z _{2) q2} Phenyl, naphthyl, (Z ² ) _q2 substituted naphthyl, representing D1-1 to D1-42, D1-81 or D1-84, where R ³ and R ⁴ are independent hydrogen atoms, C _{1 respectively.} ~ C ₆ alkyl, optionally substituted with ^{R 5} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, optionally substituted with ^{R 5} _{(C 3 to} C ₈ ) cycloalkyl, C ₂ ~ C ₆ alkenyl, optionally substituted with ^{R 5} _{(C 2 to} C ₆ ) alkenyl, C _{3 to} C ₈ cycloalkenyl, optionally substituted with ^{R 5} _{(C 3 to} C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ alkynyl, ^phenyl, phenyl substituted with (Z _{2) q2,} D1-32, or represents D1-33 or D1-34, Alternatively, ^{by R 3} to form a alkenylene chain alkylene chain or _C 2 -C ₇ of _C 2 -C ₇ together with ^{R 4,} 3 to 8 membered together with the nitrogen atom ^{to which R 3} and ^{R 4} are bonded A ring may be formed, wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and _{may be optionally substituted with C 1 to} C ₆ alkyl, oxo or tioxo. Often,
R ⁵ is halogen atom, cyano, nitro, C _{3 to} C ₈ cycloalkyl, -OR ³¹ , -S (O) _r2 R ³¹ , -C (O) OR ³¹ , -C (O) R ³² , -N. (R ³⁴ ) R ³³ , -Si (R ^32a ) (R ^32b ) R ^32c , phenyl, phenyl ^{substituted with (Z 2} ) _q2 , D1-1, D1-32, D1-33 or D1-34. carded, or when two ^{R 5} are substituted on the same carbon, two ^{R 5} oxo together, thioxo, _imino, C 1 -C _{6 alkylimino,} C 1 -C ₆ alkoxyimino Alternatively, C _{1 to} C ₆ alkylidene may be formed.
R ⁶ is optionally substituted with a hydrogen atom, C _{1 to} C ₆ alkyl, R ¹⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, R ¹⁵ (C _3). -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 15} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 15} _{(C 3} -C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 15} _(C 2 ~C ₆₎ ^{alkynyl, -C (= NOR 16) R} 17, ^phenyl, substituted with (Z _{1) q1} Represents phenyl, D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38.
R ⁷ was optionally substituted with a hydrogen atom, C _{1 to} C ₈ alkyl, R ^15b _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, R ^15b (C _3). -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 15b} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 15b} _{(C 3} -C ₈₎ represents _{cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 15b} _(C 2 ~C ₆₎ alkynyl, phenyl substituted with phenyl or ^(Z _{1) q1,}
R ^8a , R ^8b , R ^9a and R ^9b are independently hydrogen atoms, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -OR ^16a , -S (O). _r1 R ^16a , -C (O) OR ^16a , -C (O) R ^17a , -C (O) N (R ^19a ) R ^18a , -C (= NOR ^16a ) R ^17a , phenyl or (Z ¹ ) _q1 Represents phenyl substituted with
R ¹⁰ , R ¹¹ and R ¹² each independently represent a hydrogen atom or C _{1 to} C ₆ alkyl.
R ¹⁵ is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, -OR ¹⁶ , -S (O) _r1 R ¹⁶ , phenyl, phenyl ^{substituted with (Z 1} ) _q1 , D1-7, D1-11. , D1-22, D1-32, D1-33 or D1-34,
R ^15b is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, halo (C _{3 to} C ₈ ) cycloalkyl, -OR ^16b , -S (O) _r1 R ^16b , -C (O) OR ^16b ,- C (O) N (R ^18b ) R ^19b , -C (= NOR ^16b ) R ^17b , -N (R ^18b ) R ^19b , -Si (R ^32a ) (R ^32b ) R ^32c , phenyl, (Z ¹ ) phenyl substituted with _{q1, D1-32, D1-33, D1-34,} D1-36, D1-37, D1-38, or represents D1-81 or D1-84, or two ^{R 15b} are the same If the is substituted on a carbon, the two ^{R 15b} together oxo, thioxo, _imino, C 1 -C _{6 alkylimino,} C 1 -C ₆ alkoxyimino or _C 1 -C ₆ alkylidene to form May be
R ¹⁶ , R ^16a , R ^16b , R ¹⁷ , R ^17a , R ^17b , R ^18a and R ^19a each independently represent a hydrogen atom or C _{1 to} C ₆ alkyl.
R ^18b and R ^19b each independently represent a hydrogen atom, C _{1 to} C ₆ alkyl or an optionally substituted (C _{1 to} C ₆ ) alkyl with ^{R 20 , or R 18b} together with R ^19b. the by forming an alkylene chain or _C 2 -C ₇ of Arukeren chains of _C 2 -C ₇ ^becomes, may form a 3-8 membered ring together with the nitrogen atom ^{to which R 18b} and ^{R 19b} are attached, the When this alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be optionally substituted with oxo or thioxo.
R ²⁰ represents phenyl or phenyl substituted with ^{(Z 1} ) _q1.
D1-1 to D1-42, D1-81, and D1-84 each represent a ring represented by the following structure.

X ¹ represents a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl or C _{3 to} C ₈ cycloalkyl, and g2, g3 or g4 represents an integer of 2 or more. when each of ^{X 1} may be or different from each other the same as each other, when two more ^{X 1} are adjacent, the two adjacent ^{X 1} is form -CH = CHCH = CH- By doing so, a ^{6-membered ring may be formed together with the carbon atom to which each X 1} is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, or C _1. -C ₆ alkyl, halo _(C 1 ~C _{6) alkyl,} C 1 -C _{6 alkoxy,} C 1 -C _{6 alkylthio,} optionally substituted by C 1 -C ₆ alkylsulfinyl or _C 1 -C ₆ alkylsulfonyl Well,
X ^1a represents a hydrogen atom or C _{1 to} C ₆ alkyl.
X ^1b represents C _{1 to} C ₆ alkyl and represents
Z is a halogen atom, cyano, _nitro, substituted C 1 -C ₆ ^alkyl, which is optionally substituted with ^{R 45} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally in ^{R 45} Arbitrarily substituted with (C _{3 to} C ₈ ) cycloalkyl, C _{2 to} C ₆ alkyne, R ⁴⁵ _{(C 2 to} C ₆ ) alkenyl, C _{3 to} C ₈ cycloalkyne, optionally substituted with ^{R 45.} _(C 3 _{~C 8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 45} _(C 2 ~C _{6) ^{alkynyl, -OR 41, -S (O)}} r3 R 41, -C ( O) OR ⁴¹ , -C (O) R ⁴² , -C (= NOR ⁴¹ ) R ⁴² , -N (R ⁴⁴ ) R ⁴³ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-1, D1 -2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38, and q is 2 or more. When representing an integer, each Z may be the same as or different from each other.
Z ¹ represents a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy or C _{1 to} C ₆ alkoxycarbonyl, with q1 of 2 or more. When representing an integer, each Z ¹ may be the same as or different from each other.
Z ² is a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -OR ⁵¹ , -S (O) _r2 R ⁵¹ , -C (O) OR ^51a ,- Represents C (O) R ⁵² , -C (O) N (R ⁵⁴ ) R ⁵³ , -C (S) N (R ⁵⁴ ) R ⁵³ or -N (R ⁵⁴ ) R ⁵³ , where q2 is an integer of 2 or more. when referring to, each of ^{Z 2} may be different or phase from each other be identical to each other, further, when two ^{Z 2} are adjacent, the two ^{Z 2} adjacent to each -N = CHCH = CH- , -CH = NCH = CH -, - N = NCH = CH -, - CH = NN = CH -, - N = CHCH = by forming a N- or -N = CHN = CH-, each of ^{Z 2} There may form a 6-membered ring with the carbon atoms to which they are attached this case, hydrogen atoms bonded to each carbon atom forming the ring, a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, halo ( C ₁ -C _{6) alkyl,} C 1 -C _{6 alkoxy,} C 1 -C _{6 alkylthio,} may be optionally substituted by C 1 -C ₆ alkylsulfinyl or _C 1 -C ₆ alkylsulfonyl,
Z ³ is a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkylthio represents a C ₁ -C ₆ alkylsulfinyl or C ₁ -C ₆ alkylsulfonyl, when q3 represents an integer of 2 or more, each of Z ³ may be or different from each other the same as each other,
R ³¹ is a hydrogen _atom, C 1 _{~C 6} ^alkyl, optionally substituted with ^{R 35} _(C 1 ~C ₆₎ alkyl, -C ^{(O) R 37,} phenyl ^substituted with (Z _{2) q2} Represents phenyl, naphthyl or naphthyl substituted with ^{(Z 2} ) _q2,
R ³² represents a hydrogen atom, C _{1 to} C ₆ alkyl or optionally substituted (C _{1 to} C ₆ ) alkyl with ^{R 35.}
R ^32a , R ^32b and R ^32c each independently _{represent C 1 to} C ₆ alkyl.
R ³³ and ^{R 34} are each independently a hydrogen _atom, a C 1 -C ₆ alkyl, -C (O) ^{OR 36} or -C ^{(O) R 37,}
R ³⁵ represents a halogen atom, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl or phenyl.
R ³⁶ represents C _{1 to} C ₆ alkyl and represents
R ³⁷ represents a hydrogen _atom, C 1 -C ₆ alkyl, phenyl substituted with phenyl or ^(Z _{2) q2,}
R ⁴¹ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 45} _(C 1 ~C ₆₎ alkyl, ^phenyl, phenyl substituted with _{(Z 3) q3, D1-32,} D1- Represents 33 or D1-34
R ⁴² represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ⁴³ and R ⁴⁴ independently represent a hydrogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ alkoxycarbonyl or C _{1 to} C ₆ alkyl carbonyl, respectively.
R ⁴⁵ is a halogen atom, C _{3 to} C ₈ cycloalkyl, -OH, C _{1 to} C ₆ alkoxy, C _{1 to} C ₁₀ alkoxycarbonyl, -Si (R ^32a ) (R ^32b ) R ^32c , phenyl, (Z). ³ ) Representing phenyl, D1-32, D1-33 or D1-34 substituted with _q3 ^{, or if two R 45s} are substituted on the same carbon, the two R ^45s are combined. Oxo, thioxo, imino, C _{1 to} C ₆ alkyl imino, C _{1 to} C ₆ alkoxy imine or C _{1 to} C ₆ alkylidene may be formed.
R ⁵¹ represents a hydrogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C ₆₎ alkyl, phenyl, phenyl or D1-39 optionally substituted by halogen atom,
R ^51a and R ⁵² independently represent a hydrogen atom or C _{1 to} C _{6 alkyl, respectively.}
R ⁵³ and R ⁵⁴ independently represent a hydrogen atom, C _{1 to} C ₆ alkyl or C _{1 to} C ₆ alkyl carbonyl, respectively.
f5 represents an integer of 0, 1, 2, 3, 4 or 5.
f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7.
g1 and p independently represent an integer of 0 or 1, respectively.
g2, m, n, r1, r2 and r3 independently represent integers of 0, 1 or 2, respectively.
g3 represents an integer of 0, 1, 2 or 3
g4 represents an integer of 0, 1, 2, 3 or 4
q, q1, q2 and q3 independently represent integers of 1, 2, 3, 4 or 5, respectively. ] Represented by a ketone or oxime compound or a salt thereof.

Ｚ^ａ、Ｚ^ｃ及びＺ^ｅは、各々独立して水素原子、ハロゲン原子、シアノ、ニトロ、Ｃ_１〜Ｃ_６アルキル、Ｒ^４５で任意に置換された（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_８シクロアルキル、Ｒ^４５で任意に置換された（Ｃ_３〜Ｃ_８）シクロアルキル、Ｃ_２〜Ｃ_６アルケニル、Ｒ^４５で任意に置換された（Ｃ_２〜Ｃ_６）アルケニル、Ｃ_２〜Ｃ_６アルキニル、Ｒ^４５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、−ＯＲ^４１、−Ｓ（Ｏ）_ｒ３Ｒ^４１、−Ｃ（Ｏ）ＯＲ^４１、−Ｃ（Ｏ）Ｒ^４２、−Ｃ（＝ＮＯＲ^４１）Ｒ^４２、−Ｎ（Ｒ^４４）Ｒ^４３、フェニル、（Ｚ^３）_ｑ３で置換されたフェニル、Ｄ１−１、Ｄ１−２、Ｄ１−７、Ｄ１−１０、Ｄ１−１１、Ｄ１−２２、Ｄ１−３２、Ｄ１−３３、Ｄ１−３４、Ｄ１−３６、Ｄ１−３７又はＤ１−３８を表す上記〔１〕に記載のケトン若しくはオキシム化合物又はそれらの塩。 [2]
B represents the ring represented by either B-1-a or B-2-a.

Z ^a , Z ^c and ^Ze are independently substituted with hydrogen atom, halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl and R ⁴⁵ (C _{1 to} C ₆ ) alkyl, C _{3 respectively.} ~ C ₈ cycloalkyl, optionally substituted with ^{R 45} _{(C 3 to} C ₈ ) cycloalkyl, C _{2 to} C ₆ alkyne, optionally substituted with ^{R 45} _{(C 2 to} C ₆ ) alkenyl, C ₂ ~ C ₆ alkynyl, optionally substituted with ^{R 45} _{(C 2} ~ C ₆ ) alkynyl, -OR ⁴¹ , -S (O) _r3 R ⁴¹ , -C (O) OR ⁴¹ , -C (O) R ⁴² , -C (= NOR ⁴¹ ) R ⁴² , -N (R ⁴⁴ ) R ⁴³ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-1, D1-2, D1-7, D1-10, D1 The ketone or oxime compound according to the above [1] representing -11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38, or a salt thereof.

[3]
Q is the ketone compound or salt thereof according to the above [2], which represents an oxygen atom.

[4]
Q is the oxime compound or salt thereof according to the above [2], which represents ^{= NOR 7.}

[5]
A represents a hydrogen atom, C _{1 to} C ₆ alkyl or -C (O) R ² .
R ² represents C _{1 to} C ₈ alkyl and represents
R ⁶ is C _{1 to} C ₆ alkyl, optionally substituted with ^{R 15} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, -C (= NOR ¹⁶ ). Represents R ¹⁷ , phenyl, phenyl ^{substituted with (Z 1} ) _q1 or D1-32.
R ^8a represents a hydrogen atom, C _{1 to} C ₆ alkyl, -C (O) OR ^16a or -C (O) R ^17a .
R ^9a represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ^8b and R ^9b represent a hydrogen atom and represent a hydrogen atom.
R ¹⁰ , R ¹¹ and R ¹² represent a hydrogen atom.
R ¹⁵ represents a halogen atom, C _{3 to} C ₈ cycloalkyl, -OR ¹⁶ or phenyl.
R ¹⁶ , R ^16a , R ¹⁷ and R ^17a each independently _{represent C 1 to} C ₆ alkyl.
X ¹ represents halo (C _{1 to} C ₆ ) alkyl,
Z ^a , Z ^c and ^Ze were independently substituted with hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl and R ⁴⁵ , respectively. (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, -OR ⁴¹ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-7, D1-11, D1-22, D1-32 or D1 Represents -37
Z ¹ represents a halogen atom
Z ³ represents a halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy or C _{1 to} C ₆ alkyl thio.
R ⁴¹ _represents C 1 -C ₆ ^alkyl, optionally substituted with ^{R 45} _(C 1 ~C ₆₎ alkyl, phenyl, a D1-32 or D1-34,
R ⁴⁵ represents a halogen atom, phenyl or D1-34.
g2, g3 and p represent 0 and
q1 and q3 represent an integer of 1 and represent
The ketone compound or salt thereof according to the above [3], wherein g4, m and n each independently represent an integer of 0 or 1.

[6]
B represents B-1-a and represents
Z ^a represents a halogen _atom, C 1 -C ₆ alkyl or _C 1 -C ₆ alkoxy,
Z ^c is optionally substituted with halogen atoms, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, R ⁴⁵ _{(C 2 to} C ₆ ) alkenyl, C ₂ to C. ₆ Represents alkynyl, -OR ⁴¹ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-7, D1-11, D1-22, D1-32 or D1-37.
^Ze is the ketone compound according to the above [5] or a salt thereof, which represents a halogen atom or C _{1 to} C _{6 alkyl.}

[7]
A is a hydrogen atom, C _{1 to} C ₆ alkyl, optionally substituted with ^{R 5} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, optionally with ^{R 5.} substituted _(C 2 ~C ₆₎ alkenyl, substituted _C 2 -C ₆ alkynyl, optionally with ^{R 5} _(C 2 ~C _{6) ^{alkynyl, -S (O) r2 R 1}} , -C (O) OR ¹ , -C (O) SR ¹ , -C (S) OR ¹ , -C (O) R ² , -C (O) N (R ⁴ ) R ³ , -C (S) N (R ⁴ ) Represents R ³ or -S (O) ₂ N (R ⁴ ) R ³
R ¹ is C _{1 to} C ₈ alkyl, optionally substituted with ^{R 5} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, phenyl or (Z ² ) _q2. Represents phenyl substituted with
R ² was optionally substituted with _{C 1 to} C ₈ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, optionally substituted with ^{R 5} _{(C 3 to} C _8). ) _cycloalkyl, C 2 -C ₆ alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C ₈ ) _{cycloalkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ ^{alkynyl, -C (= NOR 31) R} 32, ^phenyl, phenyl substituted with (Z _{2) q2} , D1-5, D1-6, D1-8, D1-10 or D1-81.
Or R ³ _represents C 1 -C ₆ alkyl, optionally substituted with ^{R 5} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ alkenyl, phenyl substituted with phenyl or ^(Z _{2) q2} Alternatively, R ³ forms a 5- or 6-membered ring with the nitrogen atom to which ^{R 3} and R ⁴ are attached by forming an alkylene chain of _{C 4} or C ₅ together with R ^4. The alkylene chain may contain one oxygen atom or nitrogen atom and may be optionally substituted with _{C 1 to} C _{6 alkyl.}
R ⁴ represents C _{1 to} C ₆ alkyl, C _{2 to} C ₆ alkenyl or phenyl.
R ⁵ is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, -OR ³¹ , -S (O) _r2 R ³¹ , -C (O) OR ³¹ , -C (O) R ³² , -N (R). ^{34) R 33, -Si (R} 32a) (R 32b) R 32c, ^phenyl, (Z _{2) q2} at or represents phenyl or D1-1 substituted, or two ^{R 5} are on the same carbon When substituted, the two R ^5s may be combined to form C _{1 to} C ₆ alkoxyiminos.
R ⁶ is a hydrogen _atom, C 1 -C ₆ ^alkyl, which is optionally substituted with ^{R 15} _(C 1 ~C _{6) alkyl,} C 3 -C _{8 cycloalkyl,} C 2 -C ₆ alkenyl, -C (= NOR ¹⁶ ) represents R ¹⁷ , phenyl, phenyl ^{substituted with (Z 1} ) _q1 or D1-32.
R ⁷ is a hydrogen atom, C _{1 to} C ₇ alkyl, optionally substituted with ^{R 15b} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, optional with ^{R 15b.} Represents (C _{2 to C 6} ) alkenyl, C _{2 to} C ₆ alkynyl or phenyl substituted with.
R ^8a is replaced with a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -C (O) OR ^16a , -C (= NOR ^16a ) R ^17a or (Z ¹ ) _q1. Represents phenyl
R ^9a represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ^8b and R ^9b represent a hydrogen atom and represent a hydrogen atom.
R ¹² represents a hydrogen atom
R ¹⁵ represents a halogen atom, C _{3 to} C ₈ cycloalkyl or -OR ¹⁶ .
R ^15b is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, halo (C _{3 to} C ₈ ) cycloalkyl, -OR ^16b , -S (O) _r1 R ^16b , -C (O) OR ^16b ,- C (O) N (R ^18b ) R ^19b , -C (= NOR ^16b ) R ^17b , -N (R ^18b ) R ^19b , -Si (R ^32a ) (R ^32b ) R ^32c , phenyl, (Z ¹ ) Represents phenyl, D1-32 or D1-84 substituted with _q1
R ¹⁶ , R ^16a , R ¹⁷ , R ^17a and R ^17b each independently _{represent C 1 to} C ₆ alkyl.
R ^18b is optionally substituted with hydrogen atom or ^{R 20} _(C 1 ^~C ₆₎ or represents alkyl, ^{or, R 18b} is by forming an alkylene chain of _{C 5} together with ^{R 19b,} A 6-membered ring is formed with the nitrogen atom to which ^{R 18b} and R ^{19b are bonded, and this alkylene chain contains one oxygen atom.}
R ^19b represents a hydrogen atom
R ²⁰ represents the phenyl substituted with (Z ¹ ) _{q1 and represents}
X ¹ is a halogen _atom, C 1 -C ₆ alkyl, represents halo _(C 1 ~C ₆₎ alkyl or _C 3 -C ₈ cycloalkyl, g3 represents an integer 2, further two ^{X 1} is adjacent By forming -CH = CHCH = CH-, a ^{6-membered ring is formed with the carbon atom to which each X 1} is bonded, and at this time, one of the hydrogen atoms bonded to each carbon atom forming the ring is , May be replaced by a halogen atom,
X ^1a represents C _{1 to} C ₆ alkyl and represents
Z ^a , Z ^c and ^Ze are independently hydrogen atom, halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl and R ⁴⁵ . substituted on _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 45} _(C 2 ~C _{6) ^{alkynyl, -OR 41, -S (O)}} r3 R 41, -C (O) OR ⁴¹ , -C (O) R ⁴² , -C (= NOR ⁴¹ ) R ⁴² , -N (R ⁴⁴ ) R ⁴³ , phenyl, (Z ³ ) _q3 substituted phenyl, D1- Represents 2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34 or D1-37.
Z ¹ represents a halogen atom, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy or C _{1 to} C ₆ alkoxycarbonyl, and an integer in which q1 is 2 or more. When represented, each Z ¹ may be identical to each other or different from each other.
Z ² is a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -OR ⁵¹ , -S (O) _r2 R ⁵¹ , -C (O) OR ^{51a or-} represents C ^{(O) R 52,} each of ^{Z 2} may be also or different from each other the same as each other, further, when two ^{Z 2} are adjacent, the two adjacent ^{Z 2} is -N By forming = CHCH = CH−, a ^{6-membered ring may be formed together with the carbon atom to which each Z 2} is bonded. At this time, one of the hydrogen atoms bonded to each carbon atom forming the ring. May be replaced by a halogen atom,
Z ³ is a halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C ₁ to C.
₆ Alkoxy, halo (C _{1 to} C ₆ ) alkoxy or C _{1 to} C ₆ alkylthio, and when q3 represents an integer greater than ^{or equal to 2, each Z 3} may be the same or different from each other. Often,
R ³¹ is C _{1 to} C ₆ alkyl, optionally substituted with ^{R 35} _{(C 1 to} C ₆ ) alkyl, -C (O) R ³⁷ , phenyl, (Z ² ) _q 2 substituted phenyl or naphthyl. Represents
R ³² represents a C _{1 to} C ₆ alkyl or an optionally substituted (C _{1 to} C ₆ ) alkyl with ^{R 35.}
R ³³ represents −C (O) R ³⁷ .
R ³⁴ represents C _{1 to} C ₆ alkyl and represents
R ³⁵ represents, represents a halogen _atom, a C 1 -C ₆ alkylthio or phenyl,
R ³⁷ _is, C 1 -C ₆ alkyl or phenyl,
R ⁴¹ represents a hydrogen atom, C _{1 to} C ₆ alkyl, optionally substituted (C _{1 to} C ₆ ) alkyl, phenyl or D 1-32 with ^{R 45.}
R ⁴² represents C _{1 to} C ₆ alkyl and represents
R ⁴³ represents C _{1 to} C ₆ alkoxycarbonyl,
R ⁴⁴ represents a hydrogen atom,
R ⁴⁵ is a halogen atom, C _{3 to} C ₈ cycloalkyl, -OH, C _{1 to} C ₆ alkoxy, C _{1 to} C ₁₀ alkoxycarbonyl, -Si (R ^32a ) (R ^32b ) R ^32c , phenyl or D1- Represents 34
R ⁵¹ represents C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, phenyl or D 1-39 optionally substituted with a halogen atom.
R ^51a represents C _{1 to} C ₆ alkyl.
g2 represents an integer of 0, 1 or 2,
g3 and r1 independently represent integers of 0, 1 or 2, respectively.
g4, m and n independently represent integers of 0 or 1, respectively.
f7, p and r3 represent 0 and
q represents an integer of 2 or 3
q1 represents an integer of 1 or 2 and represents
q2 represents an integer of 1, 2 or 3
q3 represents an integer of 1, 2 or 3
r2 is the oxime compound or salt thereof according to the above [4], which represents an integer of 0 or 2.

[8]
B represents B-1-a and represents
Z ^a represents a halogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ alkoxy or C _{1 to} C ₆ alkyl thio.
Z ^c was optionally substituted with hydrogen atom, halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkyne, R ⁴⁵ _{(C 2 to} C _6). ) _alkenyl, C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 45} _(C 2 ~C _{6) ^{alkynyl, -OR 41, -S (O)}} r3 R 41, -C (O) OR 41, -C (O) R ⁴² , -C (= NOR ⁴¹ ) R ⁴² , -N (R ⁴⁴ ) R ⁴³ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-2, D1-7, D1-11, Represents D1-22, D1-32, D1-33, D1-34 or D1-37.
Z ^e represents a halogen _atom, C 1 -C ₆ alkyl or _C 1 -C ₆ alkoxy,
X ¹ represents a halogen atom or a halo (C _{1 to} C ₆ ) alkyl.
g3 is the oxime compound or salt thereof according to the above [7], which represents an integer of 0 or 1.

[9]
B is the ketone or oxime compound according to the above [1] representing B-1 or B-2, or a salt thereof.

[10]
B is the ketone or oxime compound according to the above [1] representing B-1, or a salt thereof.

[11]
B is the ketone or oxime compound according to the above [1] representing B-2, or a salt thereof.

[12]
B is the ketone or oxime compound according to the above [1] representing B-3, or a salt thereof.

[13]
B is the ketone or oxime compound according to the above [2] representing B-1-a, or a salt thereof.

[14]
B is the ketone or oxime compound according to the above [2] representing B-1-b, or a salt thereof.

[15]
B is the ketone compound or salt thereof according to the above [3], which represents B-1 or B-2.

[16]
B is the ketone compound or salt thereof according to the above [3], which represents B-1.

[17]
B is the ketone compound or salt thereof according to the above [3], which represents B-2.

[18]
B is the ketone compound or salt thereof according to the above [3], which represents B-3.

[19]
B is the ketone compound or salt thereof according to the above [3] and [5], which represents B-1-a.

[20]
B is the ketone compound or salt thereof according to the above [3] and [5], which represents B-1-b.

[21]
B is the oxime compound according to the above [4] representing B-1 or B-2, or a salt thereof.

[22]
B is the oxime compound or salt thereof according to the above [4], which represents B-1.

[23]
B is the oxime compound or salt thereof according to the above [4], which represents B-2.

[24]
B is the oxime compound or salt thereof according to the above [4], which represents B-3.

[25]
B is the oxime compound or salt thereof according to the above [4] and [7], which represents B-1-a.

[26]
B is the oxime compound or salt thereof according to the above [4] and [7], which represents B-1-b.

[27]
A is optionally substituted with a hydrogen atom, C _{1 to} C ₆ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkyne, optionally ^{R 5.} substituted _(C 2 ~C ₆₎ alkenyl, ketones according to optionally substituted with _C 2 -C ₆ alkynyl, or ^{R 5} _(C 2 ~C ₆₎ above or alkynyl [1] to [26] or Oxime compounds or salts thereof.

[28]
Substituted A is a hydrogen _atom, C 1 -C ₆ alkyl, optionally substituted with ^{R 5} _(C 1 ~C _{6) alkyl,} C 2 -C _{6 alkenyl,} optionally with C 2 -C ₆ alkynyl, or ^{R 5} been _(C 2 ~C ₆₎ ketone or oxime compound or salt thereof according to the representative of the alkynyl [1] to [26].

[29]
A is a hydrogen _atom, C 1 -C ₆ alkyl or optionally substituted with ^{R 5} _(C 1 ~C ₆₎ ketone or oxime compounds or their salts described above represents an alkyl [1] to [26] ..

[30]
A is a hydrogen atom, -S (O) _r2 R ¹ , -C (O) OR ¹ , -C (O) SR ¹ , -C (S) OR ¹ , -C (O) R ² , -C ( O) N (R ⁴ ) R ³ , -C (S) N (R ⁴ ) R ³ or -S (O) ₂ N (R ⁴ ) R ³ Representing the ketone according to the above [1] to [26]. Or oxime compounds or salts thereof.

[31]
A is a hydrogen atom, -C (O) OR ¹ , -C (O) SR ¹ , -C (O) R ² , -C (O) N (R ⁴ ) R ³ or -C (S) N ( R ⁴ ) The ketone or oxime compound according to the above [1] to [26] representing ^{R 3, or a salt thereof.}

[32]
A represents a hydrogen atom, -C (O) SR ¹ , -C (O) R ² or -C (O) N (R ⁴ ) R ^3, and the ketone or oxime according to the above [1] to [26]. Compounds or salts thereof.

[33]
A is the ketone or oxime compound according to the above [1] to [26] representing a hydrogen atom, or a salt thereof.

[34]
A is a ketone or oxime compound according to the above [1] to [26] or a salt thereof, which represents an _{alkyl C 1 to} C ₆ or an alkyl arbitrarily substituted with ^{R 5} _{(C 1 to} C _6).

[35]
A _is, C 2 -C ₆ alkynyl, or optionally substituted with ^{R 5} _(C 2 ~C ₆₎ ketone or oxime compound or salt thereof according to [1] to [26] above or alkynyl.

[36]
A is the ketone or oxime compound according to the above [1] to [26] representing -C (O) SR ^{1, or a salt thereof.}

[37]
A is the ketone or oxime compound according to the above [1] to [26] representing −C (O) R ^{2, or a salt thereof.}

[38]
A ^{is, -C (O) N (R} 4) ketone or oxime compound or salt thereof according to [1] to [26] representing the ^{R 3.}

[39]
A ^{is, -C (S) N (R} 4) ketone or oxime compound or salt thereof according to [1] to [26] representing the ^{R 3.}

[40]
R ¹ _is - [1] representing the C 1 -C ₈ alkyl, optionally substituted with ^{R 5} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ cycloalkyl or _C 2 -C ₆ alkenyl [ 39] The ketone or oxime compound according to [39] or a salt thereof.

[41]
R ¹ is the ketone or oxime compound according to the above [1] to [39] representing _{C 1 to} C _{8 alkyl, or a salt thereof.}

[42]
R ¹ is the ketone or oxime compound according to the above [1] to [39] representing an optionally substituted (C _{1 to} C ₆ ^{) alkyl with R 5, or a salt thereof.}

[43]
R ¹ is the ketone or oxime compound according to the above [1] to [39] representing _{C 3 to} C _{8 cycloalkyl, or a salt thereof.}

[44]
R ¹ _is, ketone or oxime compound or salt thereof according to [1] to [39], which represents the C 2 -C ₆ alkenyl.

[45]
R ² was optionally substituted with _{C 1 to} C ₈ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, optionally substituted with ^{R 5} _{(C 3 to} C _8). ) _cycloalkyl, C 2 -C ₆ alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C ₈ ) cycloalkenyl or _C 2 -C ₆ alkynyl, according to optionally substituted with ^{R 5} _(C 2 ~C ₆₎ alkynyl, or ^{-C (=} NOR ³¹⁾ above represents a ^{R 32} [1] to [44] Ketones or oxime compounds or salts thereof.

[46]
R ² is the ketone or oxime compound according to the above [1] to [44] or a salt thereof, which represents an _{alkyl C 1 to} C ₈ or an alkyl arbitrarily substituted with ^{R 5} _{(C 1 to} C _6).

[47]
R ² _is, C 3 -C ₈ cycloalkyl or ^{R 5} optionally substituted with _(C 3 ~C ₈₎ ketone or oxime compounds or their salts according to the above [1] to [44], which represents a cycloalkyl ..

[48]
R ² _is, C 2 -C ₆ alkenyl or optionally substituted with ^{R 5} _(C 2 ~C ₆₎ ketone or oxime compound or salt thereof according to [1] to [44] above alkenyl.

[49]
R ² is a ketone or oxime compound according to the above [1] to [44] representing a C _{3 to} C ₈ cycloalkenyl or a (C _{3 to} C ₈ ^{) cycloalkenyl optionally substituted with R 5, or a salt thereof.} ..

[50]
R ² is the ketone or oxime compound according to the above [1] to [44] or a salt thereof, which represents an alkynyl optionally substituted with _{C 2 to} C ₆ alkynyl or R ⁵ _{(C 2 to} C _6).

[51]
R ² is ^phenyl, phenyl substituted with _{(Z 2) q2, D1-5,} D1-6, D1-8, ketones according to the above [1] to [44], which represents the D1-10 or D1-81 Or oxime compounds or salts thereof.

[52]
R ² is the ketone or oxime compound according to the above [1] to [44] representing _{C 1 to} C _{8 alkyl, or a salt thereof.}

[53]
R ² is the ketone or oxime compound according to the above [1] to [44] representing an optionally substituted (C _{1 to} C ₆ ^{) alkyl with R 5, or a salt thereof.}

[54]
R ³ _is, C 1 -C ₆ alkyl, optionally substituted with ^{R 5} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ alkenyl, phenyl or ^(Z ₂₎ above represents phenyl substituted with _q2 The ketone or oxime compound according to [1] to [53] or a salt thereof.

[55]
R ³ _is, C 1 -C ₆ alkyl, ketone or oxime according to optionally substituted with ^{R 5} _(C 1 ~C ₆₎ alkyl or _C 2 -C above representing the ₆ alkenyl [1] to [53] Compounds or salts thereof.

[56]
R ³ is the ketone or oxime compound according to the above [1] to [53] representing phenyl or phenyl ^{substituted with (Z 2} ) _{q2, or a salt thereof.}

[57]
R ^{3, R 3} is by forming an alkylene chain of _{C 4} or _{C 5} together with ^{R 4,} forms a 5 or 6-membered ring together with the nitrogen atom ^{to which R 3} and ^{R 4} are attached, this time the alkylene chain may contain one oxygen atom or nitrogen atom, and C ₁ -C ₆ ketone or oxime compound or salt thereof according to good the substituted [1] to [53] optionally by an alkyl ..

[58]
R ⁵ is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, -OR ³¹ , -S (O) _r2 R ³¹ , -C (O) OR ^31, or phenyl, phenyl substituted with ^{(Z 2} ) _q2. The ketone or oxime compound according to the above [1] to [57] or a salt thereof.

[59]
R ⁵ is the ketone or oxime compound according to the above [1] to [57] representing a halogen atom, -OR ³¹ or -S (O) _r2 R ^{31, or a salt thereof.}

[60]
R ⁵ is the ketone or oxime compound according to the above [1] to [57] representing a halogen atom, or a salt thereof.

[61]
R ⁵ is the ketone or oxime compound according to the above [1] to [57] representing ^{−OR 31, or a salt thereof.}

[62]
R ⁵ is the ketone or oxime compound according to the above [1] to [57] representing −S (O) _r2 R ^{31, or a salt thereof.}

[63]
R ^5, when two R ⁵ are substituted on the same carbon, the two R ⁵ may be formed C ₁ -C ₆ alkoxyimino together [1] to [57] The ketone or oxime compound described in the above, or a salt thereof.

[64]
R ⁶ _is - [1] representing the C 1 -C ₆ ^alkyl, optionally substituted with ^{R 15} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ cycloalkyl or _C 2 -C ₆ alkenyl [ 63] The ketone or oxime compound according to [63] or a salt thereof.

[65]
R ⁶ is a ketone or oxime compound according to the above [1] to [63] representing phenyl, phenyl substituted with (Z ¹ ) _{q1 or D1-32, or a salt thereof.}

[66]
R ⁶ is the ketone or oxime compound according to the above [1] to [63] representing _{C 1 to} C ₆ alkyl or C _{3 to} C _{8 cycloalkyl, or a salt thereof.}

[67]
R ⁶ is the ketone or oxime compound according to the above [1] to [63] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[68]
R ⁶ is the ketone or oxime compound according to the above [1] to [63] representing _{C 3 to} C _{8 cycloalkyl, or a salt thereof.}

[69]
R ⁷ is a hydrogen atom, C _{1 to} C ₇ alkyl, optionally substituted with ^{R 15b} _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, optional with ^{R 15b.} Representing (C _{2 to} C ₆ ) alkenyl or C _{2 to} C ₆ alkynyl substituted with [1], [2], [4], [7] to [14], [21] to [63] The oxime compound described or a salt thereof.

[70]
R ⁷ represents the hydrogen atom, C _{1 to} C ₇ alkyl or _{(C 1 to} C ₆ ) alkyl optionally substituted with ^{R 15b} , the above [1], [2], [4], [7] to [ 14], the oxime compound according to [21] to [63] or a salt thereof.

[71]
R ⁷ is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [63], which represents a hydrogen atom.

[72]
R ⁷ is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [63], which represents _{C 1 to} C _{7 alkyl.}

[73]
R ⁷ represents the (C _{1 to} C ₆ ) alkyl optionally substituted with R ^15b above [1], [2], [4], [7] to [14], [21] to [63]. The oxime compound or a salt thereof according to.

[74]
R ^8a is a ketone or oxime compound according to the above [1] to [73] representing a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl or -C (O) OR ^{16a, or them.} Salt.

[75]
R ^8a is the ketone or oxime compound according to the above [1] to [73] representing a hydrogen atom or C _{1 to} C _{6 alkyl, or a salt thereof.}

[76]
R ^8a is the ketone or oxime compound according to the above [1] to [73] representing a hydrogen atom, or a salt thereof.

[77]
R ^8a is the ketone or oxime compound according to the above [1] to [73] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[78]
R ^9a is the ketone or oxime compound according to the above [1] to [77] representing a hydrogen atom, or a salt thereof.

[79]
R ^9a is the ketone or oxime compound according to the above [1] to [79] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[80]
R ¹⁵ is the ketone or oxime compound according to the above [1] to [79] representing a halogen atom, or a salt thereof.

[81]
R ¹⁵ is the ketone or oxime compound according to the above [1] to [79] representing _{C 3 to} C _{8 cycloalkyl, or a salt thereof.}

[82]
R ¹⁵ is the ketone or oxime compound according to the above [1] to [79] representing ^{−OR 16 or a salt thereof.}

[83]
R ^15b represents a halogen atom, cyano, halo (C _{3 to} C ₈ ) cycloalkyl, -OR ^16b , -S (O) _r1 R ^16b or -C (O) N (R ^18b ) R ^19b. ], [2], [4], [7] to [14], [21] to [82], the oxime compound or a salt thereof.

[84]
R ^15b represents a halogen atom, cyano, −OR ^16b or −S (O) _r1 R ^16b, as described above [1], [2], [4], [7] to [14], [21] to [82]. ] The oxime compound or a salt thereof.

[85]
R ^15b is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [82], which represents a halogen atom.

[86]
R ^15b is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [82], which represents cyano.

[87]
R ^15b is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [82], which represents ^{−OR 16b.}

[88]
R ^15b is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [82], which represents −S (O) _r1 R ^16b. ..

[89]
R ^15b represents phenyl, phenyl ^{substituted with (Z 1} ) _q1 , D1-32 or D1-84 above [1], [2], [4], [7] to [14], [21]. ~ [82] The oxime compound or a salt thereof.

[90]
R ^15b is the oxime according to the above [1], [2], [4], [7] to [14], [21] to [82], which represents phenyl or phenyl ^{substituted with (Z 1} ) _q1. Compound or salt thereof.

[91]
R ^18b is the oxime compound or salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [90], which represents a hydrogen atom.

[92]
R ^{18b is,} by ^{R 18b} is to form an alkylene chain of _{C 5} together with ^{R 19b,} to form a 6-membered ring together with the nitrogen atom ^{to which R 18b} and ^{R 19b} are attached, the time the alkylene chain oxygen The oxime compound or a salt thereof according to the above [1], [2], [4], [7] to [14], [21] to [90], which indicates that it contains one atom.

[93]
X ¹ is the ketone or oxime compound according to the above [1] to [92] representing halo (C _{1 to} C ₆ ) alkyl or C _{3 to} C _{8 cycloalkyl, or a salt thereof.}

[94]
X ¹ is the ketone or oxime compound according to the above [1] to [92] representing a halogen atom or C _{1 to} C _{6 alkyl, or a salt thereof.}

[95]
X ¹ is the ketone or oxime compound according to the above [1] to [92] representing a halogen atom, or a salt thereof.

[96]
X ¹ is the ketone or oxime compound according to the above [1] to [92] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[97]
Z ^a is the ketone or oxime compound according to the above [1] to [96] representing a halogen atom, or a salt thereof.

[98]
Z ^a is the ketone or oxime compound according to the above [1] to [96] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[99]
Z ^a is the ketone or oxime compound according to the above [1] to [96] representing _{C 1 to} C _{6 alkoxy, or a salt thereof.}

[100]
Z ^a is the ketone or oxime compound according to the above [1] to [96] representing _{C 1 to} C _{6 alkylthio, or a salt thereof.}

[101]
Z ^c was optionally substituted with hydrogen atom, halogen atom, cyano, C _{1 to} C ₆ alkyl, C _{2 to} C ₆ alkynyl, R ⁴⁵ _{(C 2 to} C ₆ ) alkynyl, phenyl, (Z ³ ) _q3. The above-mentioned [1] to [100], which represent phenyl, D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34 or D1-37 substituted with. Ketones or oxime compounds or salts thereof.

[102]
Z ^c represents a hydrogen atom, a halogen atom, _cyano, C 1 -C _{6 alkyl,} optionally substituted with C 2 -C ₆ alkynyl, or ^{R 45} _(C 2 ~C ₆₎ above [1] or alkynyl ~ [ 100] The ketone or oxime compound according to [100] or a salt thereof.

[103]
Z ^c represents phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34 or D1-37. The ketone or oxime compound according to the above [1] to [100] or a salt thereof.

[104]
Z ^c is the ketone or oxime compound according to the above [1] to [100] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[105]
Z ^c _is, C 2 -C ₆ alkynyl, or optionally substituted with ^{R 45} _(C 2 ~C ₆₎ ketone or oxime compound or salt thereof according to [1] to [100] to an alkynyl.

[106]
Z ^c is the ketone or oxime compound according to the above [1] to [100] representing phenyl or phenyl ^{substituted with (Z 3} ) _{q3, or a salt thereof.}

[107]
Z ^c is the ketone or oxime compound according to the above [1] to [100] representing D1-2, D1-7, D1-32, D1-33, D1-34 or D1-37, or a salt thereof.

[108]
Z ^c is the ketone or oxime compound according to the above [1] to [100] representing D1-32, D1-33 or D1-34, or a salt thereof.

[109]
Z ^c is the ketone or oxime compound according to the above [1] to [100] representing D1-7, or a salt thereof.

[110]
^Ze is the ketone or oxime compound according to the above [1] to [109] representing a halogen atom, or a salt thereof.

[111]
^Ze is the ketone or oxime compound according to the above [1] to [109] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[112]
^Ze is the ketone or oxime compound according to the above [1] to [109] representing _{C 1 to} C _{6 alkoxy, or a salt thereof.}

[113]
^Ze is the ketone or oxime compound according to the above [1] to [109] representing _{C 1 to} C _{6 alkylthio, or a salt thereof.}

[114]
Z ² represents a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -OR ⁵¹ or -S (O) _r2 R ^51, as described above [1] to [113]. The ketone or oxime compound described in the above, or a salt thereof.

[115]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing a halogen atom, cyano, nitro, C _{1 to} C ₆ alkyl or halo (C _{1 to} C _{6) alkyl, or a salt thereof.}

[116]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing a halogen atom or C _{1 to} C _{6 alkyl, or a salt thereof.}

[117]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing ^{-OR 51} or -S (O) _r2 R ^{51, or a salt thereof.}

[118]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing a halogen atom, or a salt thereof.

[119]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[120]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing ^{−OR 51, or a salt thereof.}

[121]
Z ² is the ketone or oxime compound according to the above [1] to [113] representing −S (O) _r2 R ^{51, or a salt thereof.}

[122]
Z ³ is the ketone or oxime compound according to the above [1] to [121] representing a halogen atom or halo (C _{1 to} C _{6) alkoxy, or a salt thereof.}

[123]
Z ³ is the ketone or oxime compound according to the above [1] to [121] representing a halogen atom, or a salt thereof.

[124]
Z ³ is the ketone or oxime compound according to the above [1] to [121] representing halo (C _{1 to} C _{6) alkoxy, or a salt thereof.}

[125]
R ³² is the ketone or oxime compound according to the above [1] to [124] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[126]
R ³² is the ketone or oxime compound according to the above [1] to [124] representing an optionally substituted (C _{1 to} C ₆ ^{) alkyl with R 35, or a salt thereof.}

[127]
R ³⁵ is the ketone or oxime compound according to the above [1] to [126] representing a halogen atom, or a salt thereof.

[128]
R ³⁵ is the ketone or oxime compound according to the above [1] to [126] representing _{C 1 to} C _{6 alkylthio, or a salt thereof.}

[129]
R ³⁵ is the ketone or oxime compound according to the above [1] to [126] representing phenyl, or a salt thereof.

[130]
R ³⁷ is the ketone or oxime compound according to the above [1] to [129] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[131]
R ³⁷ is the ketone or oxime compound according to the above [1] to [129] representing phenyl, or a salt thereof.

[132]
R ⁴¹ represents the hydrogen atom, C _{1 to} C ₆ alkyl or _{(C 1 to} C ₆ ) alkyl optionally substituted with ^{R 45} , the ketone or oxime compound according to the above [1] to [131], or the ketone or oxime compound thereof. salt.

[133]
R ⁴¹ is the ketone or oxime compound according to the above [1] to [131] representing phenyl or D1-32, or a salt thereof.

[134]
R ⁴¹ is the ketone or oxime compound according to the above [1] to [131] representing a hydrogen atom, or a salt thereof.

[135]
R ⁴¹ is the ketone or oxime compound according to the above [1] to [131] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[136]
R ⁴¹ is the ketone or oxime compound according to the above [1] to [131] representing an optionally substituted (C _{1 to} C ₆ ^{) alkyl with R 45, or a salt thereof.}

[137]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing a halogen atom, C _{3 to} C ₈ cycloalkyl, -OH or C _{1 to} C _{6 alkoxy, or a salt thereof.}

[138]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing phenyl or D1-34, or a salt thereof.

[139]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing a halogen atom, or a salt thereof.

[140]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing _{C 3 to} C _{8 cycloalkyl, or a salt thereof.}

[141]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing −OH, or a salt thereof.

[142]
R ⁴⁵ is the ketone or oxime compound according to the above [1] to [136] representing _{C 1 to} C _{6 alkoxy, or a salt thereof.}

[143]
R ⁵¹ is the ketone or oxime compound according to the above [1] to [142] representing _{C 1 to} C _{6 alkyl, or a salt thereof.}

[144]
m is the ketone or oxime compound according to the above [1] to [143] representing an integer of 0 or 1, or a salt thereof.

[145]
m is the ketone or oxime compound according to the above [1] to [143] representing an integer of 0, or a salt thereof.

[146]
m is the ketone or oxime compound according to the above [1] to [143] representing an integer of 1, or a salt thereof.

[147]
n represents the ketone or oxime compound according to the above [1] to [146] representing an integer of 0 or 1, or a salt thereof.

[148]
n represents the ketone or oxime compound according to the above [1] to [146] representing an integer of 0, or a salt thereof.

[149]
n represents the ketone or oxime compound according to the above [1] to [146] representing an integer of 1, or a salt thereof.

[150]
A pesticide containing one or more selected from the ketone and oxime compounds according to the above [1] to [149] and salts thereof as an active ingredient.

[151]
A herbicide containing one or more selected from the ketone and oxime compounds according to the above [1] to [149] and salts thereof as an active ingredient.

The compound of the present invention has excellent herbicidal activity against various weeds, high safety against target crops, and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects. It is persistent and has a light impact on the environment.
Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields and orchards.

The compound of the present invention represented by the formula (1) may exist as a keto-enol structure tautomer represented by the following formula, depending on the type and conditions of the substituent. The present invention also includes all of these structures.

また、本発明に包含される化合物は、１個又は２個以上の不斉炭素原子の存在に起因する光学活性体が存在するが、本発明は全ての光学活性体又はラセミ体を包含する。 The compounds included in the present invention may have an E-form having an E configuration and a Z-form geometric isomer having a Z configuration depending on the type of substituent. The present invention includes these E-forms, Z-forms or mixtures containing E-forms and Z-forms in arbitrary proportions, and in the present specification, these are used as a combination of wavy lines as shown below, for example. show.

In addition, the compounds included in the present invention include optically active substances due to the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.

Among the compounds included in the present invention, those which can be made into an acid addition salt according to a conventional method are, for example, hydrohalogenated acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodide. Salts of inorganic acids such as salts, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartrate acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or It can be a salt of an amino acid such as glutamic acid or aspartic acid.

Alternatively, among the compounds included in the present invention, those which can be made into metal salts according to a conventional method are, for example, alkali metal salts such as lithium, sodium and potassium, and alkaline earth metals such as calcium, barium and magnesium. It can be a salt or a salt of aluminum.

Next, specific examples of each substituent shown in the present specification are shown below. Here, n- means normal, i- means iso, s- means secondary and tert- means tertiary, and Ph means phenyl.

Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In addition, the notation of "halo" in this specification also represents these halogen atoms.

_{The notation of C a to} C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a to b carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, and the like. Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group and the like. It is selected in the range of each specified number of carbon atoms.

_{The notation of C a to} C _b alkenyl in the present specification is a linear or branched chain having a number of carbon atoms of a to b, and does not have one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-Dimethyl-2-propenyl group and the like are given as specific examples, and are selected within the range of each specified number of carbon atoms.

_{The notation of C a to} C _b alkynyl in the present specification is unsaturated having a linear or branched chain having a number of carbon atoms of a to b and having one or two or more triple bonds in the molecule. A hydrocarbon group is represented, and examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1,1-dimethyl-2-propynyl group. It is listed and selected within the range of each specified number of carbon atoms.

The notation of halo (C _{a to} C _b ) alkyl in the present specification is a linear or branched structure consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom. It represents a chain hydrocarbon group, where the halogen atoms may be the same or different from each other if they are substituted with two or more halogen atoms. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-Pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1 , 2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4,5,4-heptafluorobutyl group, nonafluorobutyl group and the like are given as specific examples. , Each is selected within the specified number of carbon atoms.

_{The notation of C a to} C _b cycloalkyl in the present specification represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure from a 3-membered ring to a 6-membered ring. Can be done. Further, each ring may be optionally substituted with an alkyl group within a specified number of carbon atoms. For example, a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like are given as specific examples, and each designated carbon atom is given. Selected in a range of numbers.

The notation of halo (C _{a to} C _b ) cycloalkyl in the present specification is a cyclic hydrocarbon having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom. It represents a group and can form a monocyclic or composite ring structure from a 3-membered ring to a 6-membered ring. In addition, each ring may be arbitrarily substituted with an alkyl group within a specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure portion, a side chain portion, or theirs. It may be both, and if it is substituted with two or more halogen atoms, those halogen atoms may be the same as each other or different from each other. For example, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Specific examples include a cyclopropyl group, a 2,2-dibromo-1-methylcyclopropyl group, a 2,2,3,3-tetrafluorocyclobutyl group, which are selected within the specified number of carbon atoms. NS.

_{The notation of C a to} C _b cycloalkenyl in the present specification represents an unsaturated hydrocarbon group having one or two or more double bonds and having a cyclic number of carbon atoms a to b, 3 A monocyclic or complex ring structure from a membered ring to a 6-membered ring can be formed. In addition, each ring may be optionally substituted with an alkyl group within a specified number of carbon atoms, and the double bond may be in the form of endo- or exo-. For example, 1-cyclopentene-1-yl group, 2-cyclopentene-1-yl group, 1-cyclohexene-1-yl group, 2-cyclohexene-1-yl group and the like are given as specific examples, and each designated carbon atom is given. Selected in a range of numbers.

_{The notation of C a to} C _b alkoxy in the present specification represents an alkyl-O— group having the above meaning consisting of a to b carbon atoms, for example, a methoxy group, an ethoxy group, an n-propyloxy group, and the like. Specific examples include an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and the like, and each is selected within a specified range of carbon atoms.

The notation of halo (C _{a to} C _b ) alkoxy in the present specification represents the haloalkyl-O- group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethoxy group, a trifluoromethoxy group, and the like. Chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro Specific examples thereof include -1,1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, and each group is selected within the specified number of carbon atoms. ..

_{The notation of C a to} C _b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylthio group, an ethylthio group, an n-propylthio group, i. Specific examples thereof include a-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, a tert-butylthio group, and the like, and each is selected within a specified range of carbon atoms.

_{The notation of C a to} C _b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylsulfinyl group.
Specific examples include ethyl sulfinyl group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group, etc., and each designation is given. It is selected in the range of the number of carbon atoms in.

_{The notation of C a to} C _b alkylsulfonyl in the present specification _{represents an alkyl-SO 2} -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, n-. Specific examples include a propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, an s-butylsulfonyl group, a tert-butylsulfonyl group, and the like, each of which has a specified range of carbon atoms. Is selected with.

_{The notation of C a to} C _b alkoxycarbonyl in the present specification represents an alkyl-OC (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methoxycarbonyl group or an ethoxycarbonyl group. Specific examples include groups, n-propyloxycarbonyl groups, i-propyloxycarbonyl groups, n-butoxycarbonyl groups, i-butoxycarbonyl groups, tert-butoxycarbonyl groups, etc., each of which has a specified range of carbon atoms. Is selected with.

_{The notation of C a to} C _b alkylcarbonyl in the present specification represents the above-mentioned meaning alkyl-C (O) -group having a number of carbon atoms of a to b, for example, an acetyl group, a propionyl group, a butyryl group. , Isobutyryl group, Valeryl group, Isovaleryl group, 2-Methylbutanoyl group, Pivaloyl group, Hexanoyl group, Heptanoyl group and the like are given as specific examples, and are selected within the range of each specified number of carbon atoms.

_{The notation of C a to} C _b alkylimino in the present specification represents an alkyl-N = group having the above-mentioned meaning consisting of a to b carbon atoms, and for example, a methylimino group, an ethylimino group, or an n-propylimino group. , I-propylimino group, n-butylimino group, i-butylimino group, s-butylimino group and the like are given as specific examples, and are selected within the range of each designated carbon atom number.

_{The notation of C a to} C _b alkoxyimino in the present specification represents the above-mentioned meaning alkoxy-N = group having a number of carbon atoms of a to b, for example, methoxyimino group, ethoxyimino group, n-propyl. Specific examples include an oxyimino group, an i-propyloxyimino group, an n-butyloxyimino group, and the like, and each is selected within a specified range of carbon atoms.

_{The notation of C a to} C _b alkylidene in the present specification represents a hydrocarbon group having a number of carbon atoms of a to b in a linear or branched chain and bonded by a double bond, for example, a methylidene group or an ethylidene. Specific examples include a group, a propylidene group, a 1-methylethylidene group, and the like, and each group is selected within the specified number of carbon atoms.

"Optionally substituted by ^{R 5} _(C a ^~C _b) alkyl" as used herein, "optionally substituted by ^{R 15} _(C a ^~C _b) alkyl" optionally substituted with ^{"R 15b} and _(C a _{~C b)} alkyl "," optionally substituted by ^{R 20} _(C a _{~C b)} alkyl "," optionally substituted by ^{R 35} _(C a _{~C b)} alkyl "or" Notations such as " _{(C a to} C _b ) alkyl optionally substituted by R ⁴⁵ " are hydrogen atoms bonded to carbon atoms by ^{any R 5} , R ¹⁵ , R ^15b , R ²⁰ , R ³⁵ or R ^45. Represents the above-mentioned alkyl group having an arbitrarily substituted number of carbon atoms consisting of a to b, and is selected in the range of each specified number of carbon atoms. At this time, when ^{two or more substituents R 5} , R ¹⁵ , R ^15b , R ²⁰ , R ³⁵ or R ⁴⁵ _{on the respective (C a to} C _b ) alkyl groups are present, the respective R ⁵ and R ^{15 are present.} , R ^15b , R ²⁰ , R ³⁵ or R ⁴⁵ may be the same or different from each other.

In the present specification, "optionally substituted by ^{R 5} _{(C a to} C _b ) cycloalkyl", "optionally substituted by ^{R 15} _{(C a to} C _b ) cycloalkyl", "optionally by ^{R 15 b".} Notations such as "substituted (C _{a to} C _b ) cycloalkyl" or "optionally substituted by ^{R 45} _{(C a to} C _b ) cycloalkyl" are any R ⁵ , R ¹⁵ , R ^{15 b} or R. ^The cycloalkyl group having the above-mentioned meaning in which the number of carbon atoms arbitrarily substituted by the hydrogen atom bonded to the carbon atom is composed of a to _b by the cycloalkyl arbitrarily substituted by _{45 (C a to C b).} It represents and is selected within the range of each specified number of carbon atoms. At this time, when ^{two or more substituents R 5} , R ¹⁵ , R ^{15 b} or R ⁴⁵ _{on each (C a to} C _b ) cycloalkyl group are present, they are R ⁵ , R ¹⁵ , R ^{15 b} or R, respectively. ^{The 45s} may be the same or different from each other, and the substitution position may be a ring structure portion, a side chain portion, or both of them.

"Optionally substituted by ^{R 5} _(C a ^~C _b) alkenyl" in the present specification, "optionally substituted by ^{R 15} _(C a ^~C _b) alkenyl", it is optionally substituted by ^{"R 15b} by the _(C a _{~C b)} alkenyl "or" optionally substituted by ^{R 45} _(C a _{~C b)} alkenyl "notation or the like, any of ^{R 5, R 15, R 15b,} or ^{R 45,} the carbon The hydrogen atom bonded to the atom is arbitrarily substituted to represent an alkenyl group having a to b carbon atoms, which is the above-mentioned meaning, and is selected in the range of each designated carbon atom number. At this time, when ^{two or more substituents R 5} , R ¹⁵ , R ^{15 b} or R ⁴⁵ _{on each (C a to} C _b ) alkenyl group are present, the respective R ⁵ , R ¹⁵ , R ^{15 b} or R ^{45 are present.} May be the same or different from each other.

"Optionally substituted by ^{R 5} _(C a ^~C _b) cycloalkenyl" herein, "optionally substituted by ^{R 15} _(C a ^~C _b) cycloalkenyl", optionally by ^{"R 15b} Notations such as "substituted (C _{a to} C _b ) cycloalkenyl" or "optionally substituted by ^{R 45} _{(C a to} C _b ) cycloalkenyl" are any R ⁵ , R ¹⁵ , R ^{15 b} or R. ^{By 45} , the hydrogen atom bonded to the carbon atom is arbitrarily substituted to represent a cycloalkenyl group having a to b carbon atoms, which is the above-mentioned meaning, and is selected in the range of each designated carbon atom number. .. At this time, when ^{two or more substituents R 5} , R ¹⁵ , R ^{15 b} or R ⁴⁵ _{on each (C a to} C _b ) cycloalkenyl group are present, they are R ⁵ , R ¹⁵ , R ^{15 b} or R, respectively. ^{The 45s} may be the same or different from each other, and the substitution position may be a ring structure portion, a side chain portion, or both of them.

Optionally substituted by ^{R 5} in this specification _(C a _{~C b)} ^alkynyl, optionally substituted by ^{R 15} _(C a _{~C b)} ^alkynyl, optionally substituted by ^{R 15b} _(C a ~ The notation such as C _b ) alkynyl or alkynyl arbitrarily substituted by ^{R 45} _{(C a to} C _b ) may be any hydrogen atom bonded to a carbon atom by ^{any R 5} , R ¹⁵ , R ^{15 b} or R ^45. Represents the above-mentioned alkynyl group in which the number of carbon atoms substituted with is a to b, and is selected in the range of each specified number of carbon atoms. At this time, when ^{two or more substituents R 5} , R ¹⁵ , R ^{15 b} or R ⁴⁵ _{on each (C a to} C _b ) alkynyl group are present, they are R ⁵ , R ¹⁵ , R ^{15 b} or R ^{45, respectively.} May be the same or different from each other.

^{"R 3,} by forming the alkenylene chain of the alkylene chain or _C 2 -C ₇ of _C 2 -C ₇ together with ^{R 4,} 3 to 8 membered together with the nitrogen atom ^{to which R 3} and ^{R 4} are bonded It indicates that a ring may be formed, and at this time, the alkylene chain or the alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom. ”As a specific example of the notation, for example, aziridine, azetidine, azetidine- 2-one, pyrrolidine, pyrrolidine-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiaziridine-2-one, thiazolidine-2-thione, imidazolidine, imidazolidine-2-one,
Imidazolidine-2-thione, piperidine, piperidine-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-one, 2H-3,4,5 , 6-Tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro -1,3-Thiazine-2-thione, thiomorpholine, perhydropyrimidine-2-one, piperazine, homopiperidin, homopiperidin-2-one, heptamethyleneimine, 1,2-dihydropyridine, 1,2-dihydropyrimidine , 1,4-dihydropyridine, 2,3-dihydro-1H-imidazole, 2,3-dihydrothiazole, 2,3-dihydrooxazole, 4,5-dihydro-1H-pyrazole, 2,5-dihydro-1H-pyrrole , 1,2,3,4-tetrahydropyridine, 1,2,3,4-tetrahydropyrimidine, 1,2,3,4-tetrahydropyridazine, etc., and each is selected within the specified number of atoms. ..

"R ^18b may form a 3- to 8-membered ring with the nitrogen atom to which ^{R 18b} and R ^19b are attached by forming an alkylene chain of _{C 2 to} C ₇ together with ^{R 19b.} At this time, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom. ”As a specific example of the notation, for example, aziridine, azetidine, azetidine-2-one, piperidine, pyrridine-2-one, Oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiazolidine-2-one, thiazolidine-2-thione, imidazolidine, imidazolidine-2-one, imidazolidine-2-thione, piperidine, piperidine-2 -On, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxadin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxadin-2 -Thion, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiadin-2-one, 2H-3,4,5,6-tetrahydro-1,3-thiadin-2-thione, thio Examples thereof include morpholin, perhydropyrimidine-2-one, piperidine, homopiperidine, homopiperidine-2-one, and heptamethyleneimine, and each is selected within a specified number of atoms.

Next, a method for producing the compound of the present invention will be described below. In the production methods A to I, A ¹ in the formula is optionally substituted with a hydrogen atom, C _{1 to} C ₆ alkyl, R ⁵ _{(C 1 to} C ₆ ) alkyl, C _{3 to} C ₈ Cycloalkyl, optionally substituted with ^{R 5} _{(C 3 to} C ₈ ), C _{2 to} C ₆ alkenyl, C _{3 to} C ₈ cycloalkenyl, optionally substituted with ^{R 5} _{(C 3 to} C ₈₎ ) cycloalkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} substituted C 2 -C ₆ alkynyl, optionally with ^{R 5} _(C 2 ~C ₆₎ alkynyl, -S (O) _r2 R ¹ , -C (O) OR ¹ , -C (S) OR ¹ , -C (O) SR ¹ , -C (S) SR ¹ , -C (O) R ² , -C (S) R ² , -C (O) N (R ⁴ ) R ³ , -C (S) N (R ⁴ ) R ³ , -S (O) ₂ N (R ⁴ ) R ³ , -P (O) (OR ¹⁾ ) ₂ or -P (S) (OR ¹ ) ₂ , and R ¹ , R ⁵ , R ² , R ³ , R ⁴ and r 2 have the same meanings as described above.

本発明化合物のうち、式（１−１−ａ）で表される化合物を、式（７−１）［式中Ｊ^ａは、ハロゲン原子、−ＯＳＯ_２Ｍｅ、−ＯＳＯ_２ＣＦ_３等の脱離基を表し、Ａ^１は前記と同じ意味を表す。］で表される化合物と反応させて、式（１−１）［式中Ｑ、Ａ^１、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物及び式（１−２）［式中Ｑ、Ａ^１、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（７−１）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。
本反応では式（１−１−ａ）で表される化合物１当量に対して、式（７−１）で表される化合物は、０．５〜５０当量の範囲で用いることができる。必要ならば、トリエチルアミン、ピリジン、４−（ジメチルアミノ）ピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン、ｎ−ブチルリチウム，リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の塩基を使用することができる。
本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method A

Among the compounds of the present invention, a compound represented by the formula (1-1-a), formula (7-1) [wherein ^{J a} is a leaving halogen _atom, -OSO 2 Me, such as -OSO ₂ CF ₃ It represents a leaving group, and A ¹ has the same meaning as described above. ], The formula (1-1) [Q, A ¹ , R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q in the formula are as described above. Represents the same meaning. ] And formula (1-2) [Q, A ¹ , R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q in the formula have the same meanings as described above. Represents. ], The compound of the present invention can be produced.
Some of the compounds represented by the formula (7-1) are known compounds, and some of them are commercially available. Further, other products can also be produced according to a known method described in the literature.
In this reaction, the compound represented by the formula (7-1) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (1-1-a). If necessary, triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium Bases such as bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxyde, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like can be used.
This reaction may be carried out without a solvent, or may use a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-. Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride. , Hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（１−１−ａ）で表される化合物のうち、式（１−１−ａ１）［式中Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物を、式（３）［式中Ｒ^７は前記と同じ意味を表す。］で表される化合物と反応させることにより、式（１−１−ａ２）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することが出来る。
式（３）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。
本反応では、式（１−１−ａ１）で表される化合物１当量に対して、式（３）で表される化合物は、０．１から１００当量の範囲で用いることができる。必要ならば、炭酸カリウム、トリエチルアミン、ピリジン、４−（ジメチルアミノ）ピリジン等の塩基を使用することができる。
本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method B

Among the compounds represented by the formula (1-1-a), the compounds represented by the formula (1-1-a1) [in the formula, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q are It has the same meaning as above. A compound represented by, Equation (3) [wherein R ⁷ have the same meanings as defined above. ] By reacting with the compound represented by the above formula (1-1-a2) [in the formula, R ⁶ , R ⁷ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q are described above. Represents the same meaning as. ], The compound of the present invention can be produced.
Some of the compounds represented by the formula (3) are known compounds, and some of them are commercially available. Further, other products can also be produced according to a known method described in the literature.
In this reaction, the compound represented by the formula (3) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (1-1-a1). If desired, bases such as potassium carbonate, triethylamine, pyridine and 4- (dimethylamino) pyridine can be used.
This reaction may be carried out without a solvent, or may use a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-. Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride. , Hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（１−１）で表される化合物のうち、式（１−１−ｂ）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表し、Ａ^３は、Ｃ_１〜Ｃ_６アルキル又はＲ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキルを表し、Ｒ^５は前記と同じ意味を表す。］で表される化合物を、加水分解することにより、式（１−１−ａ１）で表される本発明化合物を得ることができる。
本反応では、必要ならば水、メタノール、エタノール、ジクロロメタン、クロロホルム、ジエチルエーテル、テトラヒドロフラン、１，４−ジオキサン、アセトニトリル、アセトン等の溶媒を使用してもよい。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
必要ならば式（１−１−ｂ）で表される化合物１当量に対して０．１〜２０当量の塩酸、硫酸、ｐ−トルエンスルホン酸等の酸存在下で反応させることができる。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method C

Of the compounds represented by formula (1-1), the formula (1-1-b) [wherein ^{R 6, R 7, R 8a} , R 8b, R 9a, R 9b, Z, m, n and q are as defined above, ^{a 3} _is, C 1 optionally substituted with -C ₆ alkyl or ^{R 5} _(C 1 ~C ₆₎ alkyl, ^{R 5} are as defined above. ], The compound of the present invention represented by the formula (1-1-a1) can be obtained by hydrolyzing the compound.
In this reaction, if necessary, a solvent such as water, methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, acetone or the like may be used. These solvents may be used alone or in combination of two or more of them.
If necessary, the reaction can be carried out in the presence of 0.1 to 20 equivalents of an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid with respect to 1 equivalent of the compound represented by the formula (1-1-1b).
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（４）［式中Ｚ及びｑは前記と同じ意味を表し、Ａ^３は、Ｃ_１〜Ｃ_６アルキル又はＲ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキルを表し、Ｒ^５は前記と同じ意味を表す。］で表される化合物と式（５）［式中Ｊ^ａ、Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、ｍ及びｎは前記と同じ意味を表す。］で表される化合物を反応させることにより、式（１−１）で表される化合物のうち、式（１−１−ｂ）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表し、Ａ^３は、Ｃ_１〜Ｃ_６アルキル又はＲ^５で任意に置換された（Ｃ_１〜Ｃ_６）アルキルを表し、Ｒ^５は前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（４）で表される化合物の或るものは公知化合物である。それ以外のものも、例えばヘミッシェ・ベリヒテ １９８３年，１１６巻，１１９頁等に記載の公知の方法に準じて製造することができる。
式（５）で表される化合物の或るものは公知化号物である。それ以外のものも、例えばシンセシス １９８２年，３０５頁等に記載の公知の方法に準じて製造することができる。
本反応では式（４）で表される化合物１当量に対して、式（５）で表される化合物は、０．５〜５０当量の範囲で用いることができる。必要ならば、ｎ−ブチルリチウム，リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、炭酸カリウム等の塩基を使用することができる。本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、ジメチルスルホキシド、１−メチル−２−ピロリドン、１，３−ジメチル−２−イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時
間の範囲で任意に設定できる。 Manufacturing method D

Equation (4) [wherein Z and q are as defined above, ^{A 3} _is optionally substituted with C 1 -C ₆ alkyl or ^{R 5} _(C 1 ~C ₆₎ alkyl, ^{R 5} Represents the same meaning as described above. ] And the formula (5) [in the formula, ^Ja , R ⁶ , R ⁷ , R ^8a , R ^8b , R ^9a , R ^9b , m and n have the same meanings as described above. By reacting a compound represented by, among the compounds represented by formula (1-1), the formula (1-1-b) [wherein ^{R 6, R 7, R 8a} , R 8b, R ^9a , R ^9b , Z, m, n and q have the same meanings as above, and A ³ represents C _{1 to} C ₆ alkyl or optionally substituted (C _{1 to} C ₆ ) alkyl with ^{R 5.} R ⁵ has the same meaning as described above. ], The compound of the present invention can be produced.
Some of the compounds represented by the formula (4) are known compounds. Others can also be produced, for example, according to a known method described in Chemische Berichte 1983, Vol. 116, p. 119 and the like.
Some of the compounds represented by the formula (5) are publicly known products. Others can also be produced, for example, according to the known methods described on Synthesis 1982, p. 305, etc.
In this reaction, the compound represented by the formula (5) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (4). If necessary, use bases such as n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxydo, and potassium carbonate. be able to. This reaction may be carried out without a solvent, or may use a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrrolidone, 1, Polar solvents such as 3-dimethyl-2-imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, and aliphatics such as pentane and n-hexane. Hydrocarbons can be mentioned. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（９）［式中Ｚ及びｑは前記と同じ意味を表す。］で表される化合物を、式（１０）［式中Ｒ^６、Ｒ^８ａ、Ｒ^９ａ及びＱは前記と同じ意味を表す。］で表される化合物と反応させて、式（１−１−ａ３）［式中Ｒ^６、Ｒ^８ａ、Ｒ^９ａ、Ｑ、Ｚ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（９）で表される化合物の或るものは公知化合物である。それ以外のものも、例えば国際公開第２００９／０１９００５号等に記載の公知の方法に準じて製造することができる。
式（１０）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。
本反応では式（９）で表される化合物１当量に対して、式（１０）で表される化合物は、０．５〜５０当量の範囲で用いることができる。必要ならば、トリエチルアミン、ピリジン、４−（ジメチルアミノ）ピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン、ｎ−ブチルリチウム，リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の塩基を使用することができる。
本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。 Manufacturing method E

Equation (9) [Z and q in the equation represent the same meanings as described above. A compound represented by, Equation (10) [wherein ^{R 6, R 8a, R 9a} and Q are as defined above. ] Represented by is reacted with a compound with the formula (1-1-a3) [wherein ^{R 6, R 8a, R 9a} , Q, Z and q are as defined above. ], The compound of the present invention can be produced.
Some of the compounds represented by the formula (9) are known compounds. Others can also be produced according to a known method described in, for example, International Publication No. 2009/019005.
Some of the compounds represented by the formula (10) are known compounds, and some of them are commercially available. Further, other products can also be produced according to a known method described in the literature.
In this reaction, the compound represented by the formula (10) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (9). If necessary, triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium Bases such as bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxyde, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like can be used.
This reaction may be carried out without a solvent, or may use a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-. Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride. , Hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.

式（１−１−ａ）で表される化合物のうち、式（１−１−ａ４）［式中Ｒ^６、Ｒ^８ａ、Ｑ、Ｚ及びｑは前記と同じ意味を表し、Ｒ^９ａ−２は、−Ｃ（Ｏ）ＯＲ^１６ａを表し、Ｒ^１６ａは前記と同じ意味を表す。］で表される化合物を、加水分解次いで脱炭酸することにより、式（１−１−ａ５）［式中Ｒ^６、Ｒ^８ａ、Ｑ、Ｚ及びｑは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。
本反応では、必要ならば水、メタノール、エタノール、ジクロロメタン、クロロホルム、ジエチルエーテル、テトラヒドロフラン、１，４−ジオキサン、アセトニトリル、アセトン等の溶媒を使用してもよい。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
必要ならば式（１−１−ａ４）で表される化合物１当量に対して０．１〜２０当量の塩酸、硫酸、ｐ−トルエンスルホン酸等の酸又は水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の塩基存在下で反応させることができる。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method F

Of the compounds represented by the formula (1-1-a), formula (1-1-a4) [wherein ^{R 6, R 8a, Q,} Z and q are as defined ^{above, R 9a-2} Represents -C (O) OR ^16a , and R ^16a represents the same meaning as described above. A compound represented by, by hydrolysis and then decarboxylation, the formula (1-1-a5) [wherein ^{R 6, R 8a, Q,} Z and q are as defined above. ], The compound of the present invention can be obtained.
In this reaction, if necessary, a solvent such as water, methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, acetone or the like may be used. These solvents may be used alone or in combination of two or more of them.
If necessary, 0.1 to 20 equivalents of an acid such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid or sodium hydroxide, potassium hydroxide, carbonic acid with respect to 1 equivalent of the compound represented by the formula (1-1-a4). The reaction can be carried out in the presence of a base such as sodium or potassium carbonate.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（１−１−ａ）で表される化合物のうち、式（１−１−ａ６）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ^ａ、Ｚ^ｅ、ｍ及びｎは前記と同じ意味を表し、Ｊ^ｂはハロゲン原子、−ＯＳＯ_２Ｍｅ、−ＯＳＯ_２ＣＦ_３等の脱離基を表す。］で表される化合物と、式（１１）［式中Ｚ^ｃ−２はＣ_２〜Ｃ_６アルキニル、Ｒ^４５で任意に置換された（Ｃ_２〜Ｃ_６）アルキニル、フェニル、（Ｚ^３）_ｑ３で置換されたフェニルを表し、Ｊ^ｃは−Ｃ（Ｏ）ＯＨ、−Ｓｎ（Ｃ_１〜Ｃ_６アルキル）_３、−Ｂ（ＯＨ）_２等を表し、Ｒ^４５、Ｚ^３及びｑ３は前記と同じ意味を表す。］を、触媒及び塩基の存在下で反応させることにより、式（１−１−ａ７）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ^ａ、Ｚ^ｅ、Ｚ^ｃ−２、ｍ及びｎは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（１１）で表される化合物の量は、式（１−１−ａ６）で表される化合物１当量に対して０．５〜５０当量の範囲で、用いることができる。
ここで用いられる式（１１）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて製造することができる。
本反応で使用できる触媒としては、例えば、パラジウム−炭素、塩化パラジウム、酢酸パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド、テトラキス（トリフェニルホスフィン）パラジウム、［１，１’−ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド ジクロロメタン付加物等のパラジウム触媒、金属銅、酢酸銅（１価）、酢酸銅（２価）、酸化銅（１価）、酸化銅（２価）、ヨウ化銅、臭化銅、塩化銅等の銅触媒が挙げられる。これらの触媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。触媒の使用量は、式（１−１−ａ６）で表される化合物１当量に対して０．００１〜１．０当量の範囲で、用いることができる。また、１，４−
ビス（ジフェニルホスフィノ）ブタン等の配位子を触媒に対して０．００１〜１０当量の範囲で、用いることができる。
使用する塩基としては、例えば、ピリジン、ジイソプロピルエチルアミン、トリエチルアミン等の三級アミン化合物、水酸化ナトリウム水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム、リン酸三カリウム等の無機塩基等が挙げられる。塩基の使用量は、式（１１）で表される化合物１当量に対して０．１〜１０．０当量の範囲で用いることができる。
本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。使用できる溶媒としては、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method G

Of the compounds represented by the formula (1-1-a), formula (1-1-a6) [wherein ^{R 6, R 7, R 8a} , R 8b, R 9a, R 9b, Z a, Z e , M and n have the same meanings as described above, and J ^b represents a halogen atom, -OSO ₂ Me, -OSO ₂ CF _{3 and} other leaving groups. ], And formula (11) [Z ^{c-2 in the} formula is C _{2 to} C ₆ alkynyl, optionally substituted with ^{R 45} _{(C 2 to} C ₆ ) alkynyl, phenyl, (Z ³ ). Represents phenyl substituted with _q3 ^{, J c} represents -C (O) OH, -Sn (C _{1 to} C ₆ alkyl) _3, -B (OH) _2, etc., and R ⁴⁵ , Z ³ and q 3 are described above. Represents the same meaning as. ], And by reacting in the presence of a catalyst and a base, wherein (1-1-a7) [wherein ^{R 6, R 7, R 8a} , R 8b, R 9a, R 9b, Z a, Z e, Z ^c-2 , m and n have the same meanings as described above. ], The compound of the present invention can be produced.
The amount of the compound represented by the formula (11) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (1-1-a6).
Some of the compounds represented by the formula (11) used here are known compounds, and some of them are available as commercial products. In addition, other products can also be produced according to the methods described in the literature.
Examples of catalysts that can be used in this reaction include palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, and [1,1'-bis (diphenylphosphino). Ferrocene] Palladium (II) dichloride Palladium catalyst such as dichloromethane adduct, metallic copper, copper acetate (monovalent), copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, Examples thereof include copper catalysts such as copper bromide and copper chloride. These catalysts may be used alone or in combination of two or more of them. The amount of the catalyst used can be in the range of 0.001 to 1.0 equivalent with respect to 1 equivalent of the compound represented by the formula (1-1-a6). Also, 1,4-
A ligand such as bis (diphenylphosphino) butane can be used in the range of 0.001-10 equivalents with respect to the catalyst.
Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine and triethylamine, and inorganic bases such as sodium hydroxide potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate and tripotassium phosphate. Can be mentioned. The amount of the base used can be in the range of 0.1 to 10.0 equivalents with respect to 1 equivalent of the compound represented by the formula (11).
This reaction can be carried out without a solvent, but a solvent may be used. Examples of the solvent that can be used include polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, and the like. Alcohols such as 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride , Pentan, n-hexane and other aliphatic hydrocarbons. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（１−１−ａ）で表される化合物の内、式（１−１−ａ６）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ^ａ、Ｚ^ｅ、ｍ及びｎは前記と同じ意味を表し、Ｊ^ｂはハロゲン原子、−ＯＳＯ_２Ｍｅ、−ＯＳＯ_２ＣＦ_３等の脱離基を表す。］で表される化合物と、式（１２）［式中Ｘ^１及びｇ３は前記と同じ意味を表す。］を、触媒及び塩基の存在下で反応させることにより、式（１−１−ａ８）［式中Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ^ａ、Ｚ^ｅ、Ｘ^１、ｇ３、ｍ及びｎは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（１２）で表される化合物の量は、式（１−１−ａ６）で表される化合物１当量に対して０．５〜５０当量の範囲で、用いることができる。
ここで用いられる式（１２）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて製造することができる。
本反応で使用できる触媒としては、例えば、パラジウム−炭素、塩化パラジウム、酢酸パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド、テトラキス（トリフェニルホスフィン）パラジウム、［１，１’−ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド ジクロロメタン付加物等のパラジウム触媒、金属銅、酢酸銅（１価）、酢酸銅（２価）、酸化銅（１価）、酸化銅（２価）、ヨウ化銅、臭化銅、塩化銅等の銅触媒が挙げられる。これらの触媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。触媒の使用量は、式（１−１−ａ６）で表される化合物
１当量に対して０．００１〜１．０当量の範囲で、用いることができる。また、Ｎ，Ｎ’−ジメチルエチレンジアミン、Ｎ，Ｎ’−ジメチルシクロヘキサン−１，２−ジアミン等の配位子を触媒に対して０．００１〜１０当量の範囲で、用いることができる。
使用する塩基としては、例えば、ピリジン、ジイソプロピルエチルアミン、トリエチルアミン等の三級アミン化合物、水酸化ナトリウム水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム、リン酸三カリウム等の無機塩基等が挙げられる。塩基の使用量は、式（１２）で表される化合物１当量に対して０．１〜１０．０当量の範囲で用いることができる。
本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。使用できる溶媒としては、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
製造法Ａから製造法Ｈの反応は、必要であれば窒素、アルゴン等の不活性ガス雰囲気下で実施しても良い。
製造法Ａから製造法Ｈの反応において、反応終了後の反応混合物は、直接濃縮又は有機溶媒に溶解し、水洗後濃縮又は氷水に投入、有機溶媒抽出後濃縮といった通常の後処理を行ない、目的の本発明化合物を得ることができる。また、精製の必要が生じたときには、再結晶、カラムクロマトグラフ、薄層クロマトグラフ、液体クロマトグラフ分取等の任意の精製方法によって分離、精製することができる。 Manufacturing method H

Among the compounds represented by the formula (1-1-a), formula (1-1-a6) [wherein ^{R 6, R 7, R 8a} , R 8b, R 9a, R 9b, Z a, Z e , M and n have the same meanings as described above, and J ^b represents a halogen atom, -OSO ₂ Me, -OSO ₂ CF _{3 and} other leaving groups. A compound represented by, Equation (12) [wherein ^{X 1} and g3 are as defined above. ], And by reacting in the presence of a catalyst and a base, wherein (1-1-a8) [wherein ^{R 6, R 7, R 8a} , R 8b, R 9a, R 9b, Z a, Z e, X ¹ , g3, m and n have the same meanings as described above. ], The compound of the present invention can be produced.
The amount of the compound represented by the formula (12) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (1-1-a6).
Some of the compounds represented by the formula (12) used here are known compounds, and some of them are available as commercial products. In addition, other products can also be produced according to the methods described in the literature.
Examples of catalysts that can be used in this reaction include palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, and [1,1'-bis (diphenylphosphino). Ferrocene] Palladium (II) dichloride Palladium catalyst such as dichloromethane adduct, metallic copper, copper acetate (monovalent), copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, Examples thereof include copper catalysts such as copper bromide and copper chloride. These catalysts may be used alone or in combination of two or more of them. The amount of the catalyst used can be in the range of 0.001 to 1.0 equivalent with respect to 1 equivalent of the compound represented by the formula (1-1-a6). In addition, ligands such as N, N'-dimethylethylenediamine and N, N'-dimethylcyclohexane-1,2-diamine can be used in the range of 0.001 to 10 equivalents with respect to the catalyst.
Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine and triethylamine, and inorganic bases such as sodium hydroxide potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate and tripotassium phosphate. Can be mentioned. The amount of the base used can be in the range of 0.1 to 10.0 equivalents with respect to 1 equivalent of the compound represented by the formula (12).
This reaction can be carried out without a solvent, but a solvent may be used. Examples of the solvent that can be used include polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, and the like. Alcohols such as 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride , Pentan, n-hexane and other aliphatic hydrocarbons. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.
If necessary, the reaction of Production Method A to Production Method H may be carried out in an atmosphere of an inert gas such as nitrogen or argon.
In the reaction from Production Method A to Production Method H, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and then concentrated or put into ice water, and subjected to normal post-treatment such as concentration after extraction of organic solvent. The compound of the present invention can be obtained. When the need for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, and liquid chromatograph sorting.

式（１３−１）［式中Ｒ^９０は、Ｃ_１〜Ｃ_６アルコキシ、ピラゾール−１−イル、イミダゾール−１−イル等の脱離基を表し、Ａ^１、Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９
ｂ、Ｒ^９０、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物及び式（１３−２）［式中Ｒ^９０は、Ｃ_１〜Ｃ_６アルコキシ、ピラゾール−１−イル、イミダゾール−１−イル等の脱離基を表し、Ａ^１、Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｒ^９０、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物との混合物を、塩基と反応させることにより式（１−３）［式中Ａ^１、Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
使用する塩基としては、例えば、ｎ−ブチルリチウム，リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、炭酸カリウム、トリエチルアミン、ピリジン、４−（ジメチルアミノ）ピリジン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等が挙げられる。塩基の使用量は、式（１３−１）で表される化合物及び式（１３−２）で表される化合物の混合物１当量に対して０．１〜１０．０当量の範囲で用いることができる。
本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。使用できる溶媒としては、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３−ジメチル−２−イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
製造法Ｉで用いられる式（１３−１）で表される化合物及び式（１３−２）で表される化合物の混合物は、例えば反応式１に記載の製造ルートに従って製造することが出来る。 Manufacturing method I

Formula (13-1) [R ⁹⁰ in the _{formula represents a leaving group such as C 1 to} C ₆ alkoxy, pyrazole-1-yl, imidazol-1-yl, etc., and represents A ¹ , Q, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9
b , R ⁹⁰ , Z, m, n and q have the same meanings as described above. ] And formula (13-2) [R ⁹⁰ in the _{formula represents leaving groups such as C 1 to} C ₆ alkoxy, pyrazole-1-yl, imidazol-1-yl, etc., and A ¹ , Q. , R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , R ⁹⁰ , Z, m, n and q have the same meanings as described above. ] By reacting the mixture with the compound represented by the compound with a base, the formula (1-3) [A ¹ , Q, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, in the formula] n and q have the same meanings as described above. ], The compound of the present invention can be produced.
Examples of the base used include n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxydo, potassium carbonate, and triethylamine. , Pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and the like. The amount of the base used should be in the range of 0.1 to 10.0 equivalents with respect to 1 equivalent of the compound represented by the formula (13-1) and the compound represented by the formula (13-2). can.
This reaction can be carried out without a solvent, but a solvent may be used. Examples of the solvent that can be used include polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, and the like. Alcohols such as 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride , Pentan, n-hexane and other aliphatic hydrocarbons. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.
The mixture of the compound represented by the formula (13-1) and the compound represented by the formula (13-2) used in the production method I can be produced, for example, according to the production route described in the reaction formula 1.

工程１
式（１７−１）［式中Ａ^１、Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物及び式（１７−２）［式中Ａ^１、Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物の混合物は、式（１５）［式中Ａ^１、Ｚ及びｑは前記と同じ意味を表す。］で表される化合物と式（１６）［Ｑ、Ｒ^６、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、ｍ
及びｎは前記と同じ意味を表す。］で表される化合物とを、文献既知の方法、例えば、米国特許出願公開第１９８１／４２８３３４８号明細書等に記載の方法に準じて、反応させることにより製造することができる。
ここで用いられる式（１５）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて製造することができる。
また、式（１６）で表される化合物の或るものは公知化合物であり、例えば、ジャーナル オブ ザ ケミカル ソサェティー１９６５年，４３５５頁等に準じて製造することができる。
工程２
式（１７−１）で表される化合物及び式（１７−２）で表される化合物の混合物を、文献既知の公知の方法、例えば、実験化学講座 第４版（日本化学会編） １９９２年，２２巻，１２２頁等に記載の方法に準じて塩化チオニル又はオキサリルクロリド等のハロゲン化剤と反応させた後、式（１８）［式中Ｒ^９０はＣ_１〜Ｃ_６アルコキシ、ピラゾール−１−イル、イミダゾール−１−イル等を表す。］で表される化合物を、文献既知の公知の方法、例えば、実験化学講座 第４版（日本化学会編） １９９２年，２２巻，５０頁等に記載の方法に準じて反応させることにより式（１３−１）で表される化合物及び式（１３−２）で表される化合物の混合物を製造することができる。
ここで用いられる式（１８）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて製造することができる。 Reaction equation 1

Process 1
Equation (17-1) [A ¹ , Q, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q in the equation have the same meanings as described above. ] And formula (17-2) [A ¹ , Q, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, n and q in the formula have the same meanings as described above. .. Mixture of the compounds represented by] the formula (15) [wherein A ^1, Z and q are as defined above. ] And formula (16) [Q, R ⁶ , R ^8a , R ^8b , R ^9a , R ^9b , m
And N represent the same meanings as described above. ], Can be produced by reacting with a method known in the literature, for example, according to the method described in US Patent Application Publication No. 1981/4283348 and the like.
Some of the compounds represented by the formula (15) used here are known compounds, and some of them are available as commercial products. In addition, other products can also be produced according to the methods described in the literature.
Further, some of the compounds represented by the formula (16) are known compounds, and can be produced according to, for example, Journal of the Chemical Society 1965, p. 4355.
Step 2
A mixture of the compound represented by the formula (17-1) and the compound represented by the formula (17-2) can be prepared by a known method known in the literature, for example, Experimental Chemistry Course 4th Edition (edited by the Chemical Society of Japan) 1992. , Vol. 22, p. 122, etc., after reacting with a halogenating agent such as thionyl chloride or oxalyl chloride, the formula (18) [R ^{90 in the} formula is C _{1 to} C ₆ alkoxy, pyrazole-1. -Il, imidazole-1-yl, etc. ] Is reacted according to a known method known in the literature, for example, the method described in Experimental Chemistry Course 4th Edition (edited by The Chemical Society of Japan), 1992, Vol. 22, p. 50, etc. A mixture of the compound represented by (13-1) and the compound represented by the formula (13-2) can be produced.
Some of the compounds represented by the formula (18) used here are known compounds, and some of them are available as commercial products. In addition, other products can also be produced according to the methods described in the literature.

式（１−１）で表される化合物の内、式（１−１−ｂ）［式中Ａ^３、Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物と、式（１９）［式中Ｒ^１０及びＪ^ａは前記と同じ意味を表す。］で表される化合物を、反応させることにより、式（１−１−ｂ２）［式中Ａ^３、Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｒ^１０、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
式（１９）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。
本反応では式（１−１−ｂ）で表される化合物１当量に対して、式（１９）で表される化合物は、０．５〜５０当量の範囲で用いることができる。必要ならば、ｎ−ブチルリチウム，リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、炭酸カリウム等の塩基を、式（１−１−ｂ）で表される化合物１当量に対して０．５〜５０．０当量の範囲で使用することができる。本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、ジメチルスルホキシド、１−メチル−２−ピロリドン、１，３−ジメチル−２−イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２−プロパノール、エチレングリコール等のアルコール類、ジエチ
ルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ペンタン、ｎ−ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
反応温度は、−８０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 Manufacturing method J

Among the compounds represented by the formula (1-1), the formula (1-1-b) [A ³ , R ⁶ , R ⁷ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, in the formula, n and q have the same meanings as described above. A compound represented by, Equation (19) [wherein ^{R 10} and ^{J a} are as defined above. A compound represented by, by reacting the formula (1-1-b2) [wherein ^{A 3, R 6, R 7} , R 8a, R 8b, R 9a, R 9b, R 10, Z, m, n and q have the same meanings as described above. ], The compound of the present invention can be produced.
Some of the compounds represented by the formula (19) are known compounds, and some of them are commercially available. Further, other products can also be produced according to a known method described in the literature.
In this reaction, the compound represented by the formula (19) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (1-1-b). If necessary, formulate bases such as n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxyde, potassium carbonate, etc. It can be used in the range of 0.5 to 50.0 equivalents with respect to 1 equivalent of the compound represented by (1-1-b). This reaction may be carried out without a solvent, or may use a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrrolidone, 1, Polar solvents such as 3-dimethyl-2-imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, and aliphatics such as pentane and n-hexane. Hydrocarbons can be mentioned. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set to.

式（１−２）で表される化合物の内、式（１−２−ｂ）［式中Ａ^３、Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される化合物と、式（２０）［式中Ｒ^１１及びＪ^ａは前記と同じ意味を表す。］を、製造法Ｊと同様の方法で反応させることにより、式（１−２−ｂ２）［式中Ａ^３、Ｒ^６、Ｒ^７、Ｒ^８ａ、Ｒ^８ｂ、Ｒ^９ａ、Ｒ^９ｂ、Ｒ^１１、Ｚ、ｍ、ｎ及びｑは前記と同じ意味を表す。］で表される本発明化合物を製造することができる。
尚、製造法Ｊで用いる式（１−１−ｂ）で表される化合物と、製造法Ｋで用いる式（１−２−ｂ）で表される化合物は、前記の製造法Ａの方法により混合物として製造することができる。製造法Ａに記載の方法により得られた式（１−１−ｂ）で表される化合物及び式（１−２−ｂ）で表される化合物の混合物は、分離することなく製造法Ｊ及び製造法Ｋと同様の方法で反応させることにより、式（１−１−ｂ２）で表される化合物及び式（１−２−ｂ２）で表される化合物の混合物として製造することができ、式（１−１−ｂ２）で表される化合物及び式（１−２−ｂ２）で表される化合物は、該混合物より再結晶、カラムクロマトグラフィー等の任意の精製法によって分離、精製することで得ることができる。 Manufacturing method K

Among the compounds represented by the formula (1-2), the formula (1-2-b) [A ³ , R ⁶ , R ⁷ , R ^8a , R ^8b , R ^9a , R ^9b , Z, m, in the formula, n and q have the same meanings as described above. A compound represented by, Equation (20) [wherein ^{R 11} and ^{J a} are as defined above. ] By reacting in the same manner as in the production method J, the formula (1-2-b2) [A ³ , R ⁶ , R ⁷ , R ^8a , R ^8b , R ^9a , R ^9b , R ^{11 in the formula]} , Z, m, n and q have the same meanings as described above. ], The compound of the present invention can be produced.
The compound represented by the formula (1-1-b) used in the production method J and the compound represented by the formula (1-2-b) used in the production method K are prepared by the method of the above-mentioned production method A. It can be produced as a mixture. The mixture of the compound represented by the formula (1-1-b) and the compound represented by the formula (1-2-b) obtained by the method described in the production method A can be obtained from the production method J and the mixture without separation. By reacting in the same manner as in Production Method K, it can be produced as a mixture of the compound represented by the formula (1-1-b2) and the compound represented by the formula (1-2-b2). The compound represented by (1-1-b2) and the compound represented by the formula (1-2-b2) are separated and purified from the mixture by an arbitrary purification method such as recrystallization and column chromatography. Obtainable.

If necessary, the reactions of Production Methods A to K may be carried out in an atmosphere of an inert gas such as nitrogen or argon.

In the reaction of Production Method A to Production Method K, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and then concentrated or put into ice water, and subjected to normal post-treatment such as concentration after extraction of organic solvent. The compound of the present invention can be obtained. When the need for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, and liquid chromatograph sorting.

Specific examples of the active compound included in the present invention include the compounds shown in Tables 1 to 4. However, the compounds in Tables 1 to 4 are for illustration purposes only, and the present invention is not limited thereto. In the table, the substituent described as Me represents a methyl group, hereinafter, the description as Et represents an ethyl group, n-Pr and Pr-n represent a normal propyl group, and i-Pr and Pr-i. Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu-i. Is an isobutyl group, t-Bu and Butt are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen.
-N is a normal pentyl group, c-Pen and Pen-c are cyclopentyl groups, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, and n-Oct and Oct. -N represents a normal octyl group and Ph represents a phenyl group.

In the table, D1-2a, D1-2c, D1-7a, D1-7b-1, D1-7b-2, D1-7b-3, D1-7b-4, D1-10a, D1-11a, D1-11b -1, D1-11b-2, D1-11b-3, D1-11b-4, D1-22a, D1-22b-1, D1-22b-2, D1-22b-3, D1-22b-4, D1 -32a, D1-32b-1, D1-32b-2, D1-32b-3, D1-32b-4, D1-32b-5, D1-33a, D1-33b-1, D1-33b-2, D1 -33b-3, D1-33b-4, D1-34a, D1-37a, D1-37b-1, D1-108a, D1-108b-1, D1-108b-2, D1-108b-3, D1-108b -4, D1-108b-5, D1-108b-6, D1-108b-7, D1-108b-8, D1-108b-9, D1-108b-10, D1-108b-11, D1-108b-12 , D1-108b-13, D1-108b-14, D1-108b-15, D1-108b-16, D1-108b-17, D1-108b-18, D1-108b-19, D1-103-1, D1 The structures represented by −103-2, D1-103-3, D1-103-4 and A1 to A116 represent the following structures.

[Table 1]

[Table 2]

[Table 3]

[Table 4]

The compound of the present invention can be used as a herbicide for paddy fields in any of the treatment methods of soil treatment and foliage treatment under flooding. Paddy weeds include, for example, weeds of the family Potamogetonaceae represented by Potamogeton distinctus, Alisma canaliculatum, Alisma canaliculatum, and Sagittaria keis. ) Weeds, Azegaya (Leptochloa chinensis), Inubie (Echinochloa crus-galli), Tainubier (Echinochloa oryzicola), Ashikaki (Homalocenchrus japonocus) kuroguwai), bulrush (Scirpus juncoides), pulp (Scirpus nipponicus), Cyperus serotinus (Cyperus serotinus), smallflower umbrellaplant (Cyperus difformis) and Hinagayatsuri (Cyperus hakonensis) Cyperaceae represented by like (Cyperaceae) weeds, duckweed (Spirodela polyrhiza) and Lemnaceae weeds represented by Lemna paucicostata, Commelinaceae weeds represented by Murdannia keisak, etc. Weeds of the family Pontederiaceae, weeds of the family Elatinaceae represented by Elatine triandra, etc., weeds of the family Pontederia multiflora, and representatives of the Pontederia vaginalis (Ammannaia multiflora) Weeds of the family Gramineae (Oenotheraceae) represented by epilobioides, etc., Abnome (Dopatrium junceum), Ooabnomame (Gratiola japonica), Kikumo (L) imnophila sessilifolia), Azena (Lindernia procidaria) and American Azena (Lindernia)
Scrophaliaceae weeds represented by dubia), Leguminosae weeds represented by Aeschynomene indica, and American Sendangusa (Bidens fronta) and Tadosa (Asteraceae) (Composite) Weeds and the like can be mentioned.

In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any of the treatment methods of soil treatment, soil mixing treatment and foliage treatment. Examples of upland weeds include Solanaceae weeds represented by Solanum nigrum and Datara stramonium, Geraniaceae weeds represented by Granium carolinianum, and Geraniaceae. (Abution theophrasti), Malvaceae weeds represented by American goldfish (Sida spinosa), Solanaceae (Ipomoea purpurea) and other Solanaceae (Ipomoea spps.) And solanaceae (Ipomoea spps.) Solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds, solanaceae weeds Geraniaceae (Galinsoga ciliata), Geraniaceae (Cirsium)
Arvense), Noborogiku (Senecio bulgaris), Himejon (Erigeron annus) and other representatives of the family Rubiaceae (Compositae), Inugara (Rorippa indica), Noharagarashi (Lamiaceae) (Cruciferae) Weeds, Polygonum Blumei, Polygonum convolvulus, etc., Polygonaceae weeds, Polygonaceae weeds, Polygonum oleacea, Polycaceae, Lamiaceae, Lamiaceae, Lamiaceae, , Corekaza (Chenopodium ficifolia), Rubiaceae (Chenopodiaceae) weeds represented by Houkigi (Kochia scoparia), Dianthus (Stararia media), etc. Rubiaceae weeds, Commelina communis, etc., Commelinaceae weeds, Lamium amprexicaule, Lamium amplexicaule, Labiatae Lamiaceae, Lamiaceae, Lamiaceae, Lamiaceae Represented by Euphorbia supine, Euphorbia maculata, etc., Euphorbiaceae weeds, Galium spurium, Rubia akane, Rubia akane, etc. Violaceae weeds represented by, etc., and leguminosae weeds represented by American tsunoxanem (Sesbania exaltata) and Ebisugusa (Cassia obtusifolia), and octopus oxalacea ) Etc. broad leaf miscellaneous Grass (Broad-leaved weeds). Wild sorghum (Sorgham bicolor), Okusakibi (Panicum dichotomiflorum), Johnsongrass (Sorghum halepens), Inubie (Echinochloa crus-galli var. Crus-galli), barnyardgrass (barnyardgrass) , Barnyardgrass (Digitaria ciliaris), crow wheat (Avena fatua), blackgrass (Alopecurus myosuroides), barnyardgrass (Eleusine indica), Enocologsa (Setaria viridis) Examples thereof include weeds (Graminaceous weeds) and grass weeds (Cyperaceous weeds) represented by nutsedge (Cyperus rotundus, Cyperus esculentus) and the like.

In addition to agricultural and horticultural fields such as paddy fields, upland fields and orchards, the compound of the present invention can be used for soil treatment, soil mixing treatment and foliage treatment in non-agricultural land such as turf, athletic fields, open areas, roadsides, and railroad tracks. It can also be used in the processing method of. The weeds include Poa annua, Taraxacum office, Erigeron sumatrensis, Cardamine flexuosa, Cardamine flexuosa, Cardamine flexuosa, in addition to the weeds mentioned in the field and orchard weeds. (Hydrocotile sibthorpioides), Cardamine flexuosa, Kyllinga brevifolia, Equisetum arvense and the like.

The compound of the present invention may be mixed and applied with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying, if necessary.

In particular, by applying the mixture with other herbicides, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicide spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicide effect can be expected. At this time, it is possible to combine with a plurality of known herbicides at the same time.

Preferred herbicides to be used in combination with the compound of the present invention include, for example, acetochlor (generic name), asifluorphen (generic name), acronifen (generic name), and alachlor (alachlor / generic name). Generic name), alloxydim (generic name), alloxydim-sodium (generic name), amethrin (generic name), amicarbasone (generic name), amidosulfuron (generic name), Aminocyclopyracrol (generic name), salts and esters of aminocyclopyracrol (aminocyclopyraclor-salts and herbicide), aminopyralide (generic name), salts and esters of aminopyralide (aminopyralid). Phosmethyl (amiprophos-methyl / generic name), amitrol (generic name), anilophos (anilofos / generic name), ashram (assulam / generic name), atrazine (gene / generic name), azafenidin (generic name) , Azimsulfuron (generic name), beflubutamide (generic name), benazolin ethyl (generazolin-ethyl / generic name), bencarbazone (generic name), benfurlarin (generalin) benefuralin Benzulfuron-methyl (generic name), benzulfuron-methyl (generic name), benzlide (generic name), ventazone (generic name), sodium bentazone (bentazone-sodium / generic name), salt of bentazone (bentazone-salt). ), Benthiocarb (generic name), benzfendizone (generic name), benzobicyclon (generic name), benzophenap (generic name), bialaphos (generic name), vialaphos (generic name) Natriu Mu (bialaphos-sodium / generic name), bicyclopyrone (generic name), biphenox (genex / generic name), bispiribac (generic name), bispiribac-sodium (generic name), bromacil bromacil (generic name), bromobutide (generic name), bromophenoxym (generic name), bromoxynil (generic name), bromoxynyl salts and esters (blomoxynil-saltsators rusters) Name), butafenacil (generic name), butamiphos (generic name), butenachlor (generic name), butraline (generic name), butroxydim (generic name), butylate (generic name) , Cafenstrole (generic name), carbetamide (generic name), carfentrazone-ester, chromethoxyphen (generic name), chromethoxynil (generic name), clomethoxynil (generic name) Chloramben-salts and esters, chloransulam-methyl (generic name), chlorflurenol-methyl (generic name), chloridazon (generic name) , Chlorimuron-ester (generic name), chlorobromron (generic name), chlorotroluron (generic name), chloroxuron (generic name), chlorphthalim (generic name), chlorphtalim Fam (chlorpropham / generic name), chloro IPC (chlorpropham / generic name), chlorsulfuron (generic name), chlortaldimethyl (chlorther-dimethyl / generic name), chlorthiam Butyl (generic name), cinidone ethyl (cinidon-ester / generic name), symmethylin (generic name), cinosulfuron (generic name), cletodim (generic name), clodinahop (generic name) Clodinahop-propargyl (generic name), chromazone (generic name), chromeprop (generic name), clonylid (generic name), salts and esters of clopyralids. CNP (generic name), cumylron (generic name), cyanazine (generazin / generic name), cycloate (cycloate / generic name), cyclopyrimorate (generic name, SW-065 / test name), cyclosul Famlon (generic name), cycloxidim (generic name), cyhalohop-butyl (generic name), DAH-500 (test name), dalapon (generic name), ester (dazomet /) Generic name), desmedipham (generic name), desmethrin (generic name), dicamba (generic name), dicamba-salts and esters, diclobenyl (generic name) , Diclohop (general name), diclohop methyl (diclop-methyl / generic name), dichloroprop (dichlolrop / generic name), dichlorprop-salts and esters, P dichloroprop-salts and esters. (Dicholrop-P / generic name), salts and esters of P-dichloroprop (diclolrop-P-salts and esters), dicloslum (generic name), difenzocoat (generic name), difluphenican (difluphenican) , Diflufenzopyr (generic name), diflufenzopyr sodium (di) flufenzopyr-sodium (generic name), dimepipelate (generic name), dimethametrin (generic name), dimethachlor (generic name), dimethenamide (genemid) dimethenamide (generic name) dimethenamide (generic name) , Dimethipin / generic name, dinitroamine (generic name), dinoseb (geneb / generic name), dinoterb (generic name), DNOC / generic name, diphenamide (generic name), diquat / Generic name), dithiopyll (generic name), diuron (generic name), DSMA / generic name, dymron (generic name), endtal (endothal / generic name), EPTC / generic name, esprocarb (/ generic name) esprocarb (generic name), ethalflularin (generic name), etamethsulfuron-methyl (generic name), etofumestate (generic name), ethofumestate (generic name), etobenzanid (generous name / generic name) / Generic name), Frazasulfuron (generic name), phenoxaprop (genexaprop / generic name), phenoxaprop-ethyl (generic name), phenoxasulfone (generic name), fennoxano Trion (generation / generic name), fentrazamide (generic name), flamprop (flamplop / generic name), flazasulfuron (generic name), floraslum (generic name), fluazihop (generic name) , Fluazihopbutyl (generic name), fluazolate (generic name), sodium flucarbazone-sodium (generic name), flucetosulfuron (generic name), fluchloralin (generic name) First name), flufenacet / Glyphosate (generic name), flufenpyl-ethyl (generic name), flumethulum (generic name), flumicrolac-pentyl (generic name), flumioxazine (generic name), fluometuron (fluom) / Generic name), Fluoroglycophen-ethyl (generic name), flupyrsulfuron (generic name), flupoxam (generic name), flurenol (generic name), fluridone (generic name) ), Flurochloridone (generic name), fluroxypyr (generic name), fluloxypyr-esters, fluprimidol (generic name), flutamone (general name), flulutamon (generic name) (Fluthiacet-methyl / generic name), fomesafen (generic name), foramsulfuron (generic name), phosamine (generic name), glufosinate (generic name), glufosinate ammonium (glufosinate) Glyphosate (generic name), glyphosate (generic name), glyphosate ammonium (general name), glyphosate isopropylamine (glyphosate-iso-propylammium / generic name), glyphosate potassium (general name) glyphosate-potassi (Glyphosate-sodium / generic name), glyphosate-trimesium (generic name), halouxifen (generic name), salts and esters of haloxifen (halauxifen-saltsafens), halo Generic name), halosulfuron (generic name), halosulfuron-methyl (generic name), haloxyhop (generic name), haloxyhop methyl (generic name) haloxyfop-methyl / generic name, hexadinone (generic name), imazamethabensmethyl (generic name), imazamox (generic name), imazapic (generic name), imazapic (generic name), imazapic (generic name) Common name), imazetapyr (generic name), imazaquin (generic name), imazosulfuron (generic name), indanofan (generic name), indazifram (generic name) iodosulfuron-methyl-sodium (generic name), ioxinil octanoate (generic name), ioxinil-salts and esters, ipfencarbazone (generic name), ipfencarbazone (generic name) Name), isouron (generic name), isoxaben (generic name), isoxaflutole (generic name), carbutyrate (generic name), lactofen (generic name), lenacil / Generic name), linuron (generic name), maleic hydrazide (generic name), MCPA (generic name), MCPA salts and esters (MCPA-salts and esters), MCPB
(Generic name), MCPB salts and esters (MCPB-salts and esters), mecoprop (mecoprop, MCPP / generic name), mecoprop-salts and esters, P mecoprop (mecoprop-P, MCPP- P / generic name), salt and ester of P mecoplop (mecoprop-P-salts and esters), mephenacet (generic name), mefluidide (generic name), mesosulfuron-methyl (generic name), Mesotrione (generator / generic name), metam (metam / generic name), metamihop (metamifop / generic name), metamitron (genemitron / generic name), metazachlor (generic name), methabenzalon (general name) Name), metazosulfuron (generic name), methiozolin (generic name), methyl azide (generic name), methyl bromide (generic name), methyl dimeron (generic name) Methyl compound (generic name), methylbenzuron (generic name), methylochlor (generic name), S methylochlor-S / generic name, metoslum (generic name), methylbudin (metribdin) / Generic name), metulfuron-methyl (generic name), metoxuron (generic name), molinate (generate / generic name), monolinuron (generic name), monosulfuron (generic name), monos Luflonmethyl (monosulfuron-methyl / generic name), MSMA / generic name, naproanilide (generic name), napropamide (generic name), naptalam (naptalam / generic name), naptalum sodium (naptalum name) ), Nebulon (generic name), Nicosulfuron (nicosul) furon (generic name), norflurazon (generic name), OK-701 (test name), oleic acid (generic name), orbencarb (generic name), orthosulfamuron (generic name) , Oryzalin (generic name), oxadiargyl (generic name), oxadiazone (generic name), oxasulfuron (generic name), oxazichromefone (generic name), oxyfluorphen (generic name) ), Paracoat (generic name), pelargonicicic acid (generic name), pendimethalin (generic name), penoxyslam (generic name), pentanochlor (generic name), pentoxazone (pent) / Generic name), petoxamide (generic name), phenmedifam-ethyl (generic name), picloram (generic name), picloram-salts and esters, picolinafen / Generic name), pinoxaden (generic name), piperophos (generic name), pretilachlor (generic name), primisulfuron-methyl (generic name), prodiamine (generic name) , Profluazole (generic name), profoxydim (generic name), promethon (promethon / generic name), promethrin (generic name), propachlor (generic name), propanil (generic name) ), Propazinehop (generic name), propazine (generic name), profam (generic name), propisochlor (generic name), propoxycarbazone sodium (generic name) , Propazine
ulfuron (generic name), propizzamide (generic name), pursulfocurb (generic name), prosulfuron (generic name), pyraclonil (generic name), pyraflufenethyl (generic name) Pyrazosulfone (generic name), pyrazosulfotle (generic name), pyrazolynate (generic name), pyrazosulfuron (generic name), pyrazosulfuron-ethyl (generic name), simazine (generic name), simazine , Pyribenoxim (generic name), pyribuchicarb (generic name), pyridafol (generic name), pyridate (generic name), pyriftalid (generic name), pyriminobacmethyl (pyriminobac) Generic name), pyrimisurfan (generic name), pyrithiobac-sodium (generic name), pyroxa sulfone (generic name), pyroxyslam (generic name), quinchlorac / Generic name), kimmerac (generic name), quinoclamine (generic name), quizalohop (generic name), quizalofop-ethyl (generic name), quizalohop tefril (generic name) tefuryl / generic name), P quizalohop-P / generic name, P quizalohop ethyl (generic name), P quizalohop-P-tefuryl (generic name), Rimsulfuron (generic name), saflufenacil (generic name), setoxydim (generic name), siduron (generic name), simazine (generic name), simazine (generic name), simethrin (generic name) -261 (test name), sulcotrione (generic name), sulfone tranzone (Sulfentrazone / generic name), sulfometuron-methyl (generic name), sulfosulfuron (generic name), TCBA (2,3,6-TBA / generic name), TCBA salts and esters (sulfofuron / generic name) 2,3,6-TBA-salts and esters), TCTP (chlorthal-dimethyl, tetorachromothiophene / generic name), tebutam (generic name), tebutiuron (generic name), tefryltrion (generic name) , Tembotrione (generic name), teplaroxydim (generic name), terbacill (generic name), turbumeton (generic name), terbutylazine (generic name), turbutrin (generic name), turbutrin (generic name) , Tetrapion (generic name), tenylchlor (generic name), thiazafluron (generic name), thiazopyr (generic name), thijiazimin (generic name) , Thiencarbazone-methyl (generic name), thifensulfuron-methyl (generic name), tolpyrlate (generic name), topramison (generic name), tralcoxydyl (generic name) ), Triafamon (generic name), triallate (generic name), triasulfuron (generic name), triazifram (generic name), tribenuron-methyl (generic name), Triclopyr (generic name), triclopyr-salts and esters, tridiphane (generic name), trietazine (generic name), trifludimoxazine (trifludimoxin) bird Floxysulfuron (generic name), triflularin (generic name), triflusulfuron-ester (generic name), tritosulfuron (generic name), 2,4-PA (generic name) ), 2,4-PA salts and esters (2,4-PA-salts and esters), 2,4-DB (generic name), 2,4-DB salts and esters (2,4-DB-salts) And esters) and the like. These components can be used alone or in combination of two or more, and the ratio when mixed can be freely selected.

Examples of the drug damage reducing agent include AD-67, benoxacor (generic name), cloquintocet-mexil (generic name), cyomerinil (generic name), dichlormid (generic name), and the like. Dicyclonone (generic name), cyprosulfamide (generic name), dietate (generoate / generic name), DKA-24, dimron (generic name), fenchlorazole-ethyl (generic name) ), Fenchlorim (generic name), hexim (HEXIM / generic name), flurazole (generic name), fluxophenim (generic name), furilazole (generic name), isoxadiphen (generic name) Isoxadifen-ethyl (generic name), MCPA, mecoprop (generic name), mefenpyr (generic name), mefenpyr-ethyl (generic name), mefenpil diethyl (generic name) mefenpyr-diethyl (generic name), mephenate (generic name), MG-191, NA (Naphthical anhydride), OM (Octamethylene-diamine), oxabetrinil (generic name), PPG-1292 Can be mentioned. These components can be used alone or in combination of two or more, and the ratio when mixed can be freely selected.

When the compound of the present invention is applied as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreeze agent, a binder, and a solid. Add a binder, a disintegrant, a decomposition inhibitor, etc., and use it as a formulation of any dosage form such as a wettable powder, an emulsion, a flowable agent, a dry flowable agent, a liquid agent, a powder, a granule, or a gel agent. be able to. Further, from the viewpoint of labor saving and safety improvement, the above-mentioned preparation of any dosage form can be encapsulated in a water-soluble package and provided.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulsite, zeolite and diatomaceous earth, and inorganic substances such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicate.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. Examples include acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

These solid and liquid carriers may be used alone or in combination of two or more.

Surfactants include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters and polyoxyethylene sorbitan. Nonionic surfactants such as fatty acid esters, alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, Anionic surfactants such as salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrene sulfonates, Examples thereof include cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric surfactants such as amino acid type and betaine type.

The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by mass with respect to 100 parts by mass of the pharmaceutical product of the present invention. In addition, these surfactants may be used alone or in combination of two or more.

The compound of the present invention may be mixed and applied with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying, if necessary.

In particular, by applying the mixture with other herbicides, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicide spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicide effect can be expected. At this time, it is possible to combine with a plurality of known herbicides at the same time.

The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, cultivated crop, etc., but generally, the amount of the active ingredient is appropriately about 0.005 to 50 kg per hectare (ha).

Next, a compounding example of the pharmaceutical product when the compound of the present invention is used is shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by mass. Wettable powder 0.1 to 80 parts of the present invention Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Other examples include anticaking agents and decomposition inhibitors.
Emulsion Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Other examples include spreading agents and decomposition inhibitors.
Flowable agent 0.1 to 70 parts of the compound of the present invention Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Other examples include antifreeze agents and thickeners. Be done.
Dry flowable agent 0.1 to 90 parts of the compound of the present invention Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder, a decomposition inhibitor and the like. ..
Liquids Compounds of the present invention 0.01 to 70 parts Liquid carriers 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreeze agents and spreading agents.
Granules 0.01 to 80 parts of the compound of the present invention Solid carrier 10 to 99.99 parts Others 0 to 10 parts Other examples include binders, decomposition inhibitors and the like.
Powders Compounds of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Other examples include anti-drift agents and anti-decomposition agents.

When using, the above-mentioned preparation is sprayed as it is or diluted 1 to 10,000 times with water.

Examples of preparations Next, examples of pesticide preparations containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these. In the following formulation examples, "parts" means parts by mass.
[Formulation Example 1] Wettable compound No. 1 of the present invention. 1-001 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
Carplex # 80 Part 2 (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and pulverized to obtain a wettable powder.
[Formulation Example 2] Emulsion Compound No. 2 of the present invention. 1-001 5 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.
[Formulation Example 3] Flowable agent Compound No. 3 of the present invention. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name)
Lunox 1000C 0.5 part (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
After uniformly mixing 0.02 parts of xanthan gum and 64.48 parts of water or more, wet pulverization is performed to obtain a flowable agent.
[Formulation Example 4] Dry flowable agent Compound No. 4 of the present invention. 1-001 75 parts High Tenor NE-15 5 parts (anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries, Ltd. trade name)
Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed and kneaded, granulated by an extrusion type granulator, and dried to obtain a dry flowable agent.
[Formulation Example 5] Granules Compound No. 5 of the present invention. 1-001 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and crushing, add a small amount of water, stir and mix and knead, granulate with an extrusion type granulator, and dry to obtain granules.

Hereinafter, the present invention will be described in more detail by specifically describing synthetic examples and test examples of the ketone or oxime compound represented by the formula (1) used as the active ingredient in the herbicide of the present invention as examples. However, the present invention is not limited thereto.

For the medium pressure preparative liquid chromatography described in the synthesis example, a medium pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column) was used.

A Discoverer manufactured by CEM was used as the microwave synthesizer, and a closed container dedicated to the device was used as the reaction vessel. For high performance liquid chromatography, a 10AVP system manufactured by Shimadzu Corporation was used.

The proton nuclear magnetic resonance chemical shift values of example, using _Me 4 Si (tetramethylsilane) as the reference substance, was measured at 300 MHz. Moreover, the solvent used for the measurement is described in the following synthesis example. The symbols in the proton nuclear magnetic resonance chemical shift values of the examples have the following meanings.
s: singlet, brs: broad singlet, d: doublet, t: triplet, m: multiplet

Synthesis Example Synthesis Example 1: Production of 2-mesityl-3-methoxy-5-{2- (methoxyimino) propyl} cyclopenta-2-enone (Compound No. 1-001) 2-mesityl-3-methoxycyclopenta- A mixed solution of 0.5 g of 2-enone and 10 ml of tetrahydrofuran was cooled to −78 ° C. under a nitrogen atmosphere, and then lithium diisopropylamide (a mixed solution of about 1.5 mol / L n-hexane and tetrahydrofuran, manufactured by Tokyo Kasei Kogyo Co., Ltd.). ) 2.3 ml was added dropwise. After completion of the dropping, the reaction mixture was stirred at the same temperature for 30 minutes. After completion of stirring, 0.34 g of 1-chloropropane-2-one O-methyloxime was added to the reaction mixture. After completion of the addition, the reaction solution was stirred at −78 ° C. for 20 minutes, heated to room temperature, and stirred at the same temperature for 15 hours. After completion of the reaction, the reaction mixture was added to ice water and extracted with 20 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate [1: 1 (volume ratio, the same applies hereinafter)], and 76 mg of the target product was used as a white solid. Obtained.
Melting point 92-98 ° C

Synthesis Example 2: Production of 3-Hydroxy-2-mesityl-5- (2-oxopropyl) cyclopenta-2-enone (Compound No. 2-001) 2-Mesityl-3-methoxy-5-{2- (methoxy) To a mixed solution of 60 mg of imino) propyl} cyclopenta-2-enone and 1 ml of acetone, 1 ml of a 2M aqueous hydrochloric acid solution was added. After completion of the addition, the reaction mixture was stirred at 50 ° C. for 4 hours. After completion of the reaction, 5 ml of ethyl acetate was added to the reaction mixture, and the organic layer was taken out. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 56 mg of the target product as a white solid.
Melting point; 183-185 ° C

Synthesis Example 3: Production of 3-Hydroxy-2-methicyl-5-{2- (methoxyimino) propyl} cyclopenta-2-enone (Compound No. 1-002) 3-Hydroxy-2-methicyl-5- (2) To a mixed solution of 50 mg of -oxopropyl) cyclopenta-2-enone, 2 ml of methanol and 1 ml of water, 24 mg of O-methylhydroxylamine hydrochloride was added. After completion of the addition, the reaction mixture was stirred at 50 ° C. for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. After adding 10 ml of ethyl acetate to the obtained residue, it was washed with water. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 31 mg of the target product as a white solid.
Melting point; 170-173 ° C

Synthesis Example 4: Production of 2-methicyl-4- {2- (methoxyimino) propyl} -3-oxocyclopenta-1-ene-1-yl pivalate (Compound No. 1-004) 3-hydroxy-2- To a mixed solution of mesityl-5- {2- (methoxyimino) propyl} cyclopenta-2-enoone (150 mg) and dichloromethane (5 ml), 139 mg of triethylamine, 6 mg of 4-dimethylaminopyridine and 186 mg of pivalic anhydride were sequentially added. After completion of the addition, the reaction mixture was stirred at room temperature for 15 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture, and the mixture was extracted with 10 ml of chloroform. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. After distilling off the solvent, the obtained residue was purified by medium pressure preparative liquid chromatography eluting with hexane-ethyl acetate (2: 1) to obtain 150 mg of the desired product as a colorless oil.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ6.85-6.81 (m, 2H), 3.87-3.82 (m, 3H), 3.70-2.18 (m, 8H) ), 2.15-1.78 (m, 9H), 1.08 and 1.06 (s, 9H)

Synthesis Example 5: Production step 1 of 2- (4-bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopenta-2-enone (Compound No. 7-027) : Production of 5-bromo-2-iodo-1-methoxy-3-methylbenzene 15.7 g of 4-bromo-2-methoxy-6-methylaniline synthesized by the method described in International Publication No. 2005/028479, concentrated hydrochloric acid. A mixed solution of 130 ml and 130 ml of water was cooled to 0 ° C. 5.5 g of sodium nitrite was added to the mixed solution while maintaining a temperature of 5 ° C. or lower, and the mixture was further stirred for 30 minutes. Then, a mixed solution of 13.3 g of potassium iodide and 65 ml of water was added to the reaction solution while maintaining a temperature of 5 ° C. or lower, and then the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the reaction solution was extracted with 200 ml of 1,2-dichloroethane. The obtained organic layer was washed in the order of 200 ml of a 1 mol / L sodium hydroxide aqueous solution, 200 ml of a 1 mol / L sodium sulfite aqueous solution, 200 ml of a 1 mol / L hydrochloric acid aqueous solution, and 200 ml of saturated sodium hydrogen carbonate. Subsequently, the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (10: 1) to obtain 10.3 g of the desired product as a brown solid.
Melting point; 72-75 ° C
Step 2: Preparation of (4-Bromo-2-methoxy-6-methylphenyl) (Fran-2-yl) Methanol A mixed solution of 5 g of 5-bromo-2-iodo-1-methoxy-3-methylbenzene and 50 ml of tetrahydrofuran. Was cooled to −70 ° C. under a nitrogen atmosphere. To the mixed solution, 8.1 ml of isopropylmagnesium chloride lithium chloride complex (about 1 mol / L tetrahydrofuran solution, manufactured by Tokyo Chemical Industry Co., Ltd.) and then 4.6 ml of isopropylmagnesium chloride (about 1 mol / L tetrahydrofuran solution, manufactured by Tokyo Chemical Industry Co., Ltd.) were sequentially added. After adding and stirring for 30 minutes, a mixed solution of 2.2 g of furfural and 20 ml of tetrahydrofuran was added. After completion of the addition, the temperature was raised to room temperature, and the mixture was stirred at the same temperature for 15 hours. After completion of the reaction, 50 ml of a saturated aqueous solution of ammonium chloride was added to the reaction solution, and the solvent was distilled off under reduced pressure until the amount was reduced to half. The obtained residue was extracted with 30 ml of ethyl acetate, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (20: 1-10: 1 gradient) to obtain 4.6 g of the desired product as a yellow oil. rice field.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.38-7.34 (m, 1H), 7.00 (brs, 1H), 6.97 (brs, 1H), 6.37-6. 20 (m, 1H), 6.03-5.92 (m, 2H), 3.83 (s, 3H), 4.21 (d, J = 10.8Hz, 1H), 2.31 (s, 3H)
Step 3: Preparation of 5- (4-Bromo-2-methoxy-6-methylphenyl) -4-hydroxycyclopenta-2-enone (4-Bromo-2-methoxy-6-methylphenyl) (Fran-2- Il) A mixed solution of 2.6 g of polyphosphate, 10 ml of acetone and 4 ml of water was added to a mixed solution of 4.6 g of methanol, 35 ml of acetone and 10 ml of water, and the mixture was stirred at 55 ° C. for 1 hour. After completion of the reaction, the solvent was distilled off by reducing the pressure until the volume of the reaction mixture was reduced to half. After adding 30 ml of water to the obtained residue, the mixture was extracted with 30 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 4: 1 to 1: 2) to obtain 3.1 g of the desired product as a brown oil. rice field.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.52-7.46 (m, 1H), 7.02 (brs, 1H), 6.84 (brs, 1H), 6.36-6. 28 (m, 1H), 5.09-5.01 (m, 1H), 3.86-3.52 (m, 5H), 2.36 (s, 3H)
Step 4: Production of 2- (4-Bromo-2-methoxy-6-methylphenyl) cyclopenta-4-ene-1,3-dione In a mixed solution of 1.6 g of chromium oxide (trivalent) and 8.6 ml of water. , 1.1 ml of concentrated sulfuric acid was added under ice-cooling. The reaction solution was added to a separately prepared mixed solution of 5- (4-bromo-2-methoxy-6-methylphenyl) -4-hydroxycyclopent-2-enoone (3.1 g) and 28 ml of acetone by ice cooling. It was added and stirred for 25 minutes. After completion of the reaction, 30 ml of isopropyl alcohol was added to the reaction solution, and then the solvent was distilled off under reduced pressure. To the obtained residue, 30 ml of ethyl acetate was added, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with diisopropyl ether to obtain 1.8 g of the target product as a yellow solid.
Melting point; 104-107 ° C
Step 5: Preparation of 2- (4-Bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopenta-2-enonone 2- (4-Bromo-2-methoxy-) To a mixed solution of 1.8 g of 6-methylphenyl) cyclopenta-4-ene-1,3-dione and 30 ml of N, N-dimethylformamide, 1.7 g of potassium carbonate and 0.85 g of methyl acetoacetate were sequentially added to room temperature. Was stirred for 15 hours. After completion of the reaction, a 1 mol / L hydrochloric acid aqueous solution was added to the reaction solution to adjust the pH to 3, and the mixture was extracted with 30 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. To the obtained residue, 20 ml of methanol and 5 ml of water were added, 1 g of potassium hydroxide was further added, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 20 ml of a 1 mol / L hydrochloric acid aqueous solution was added, and the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.8 g of the target product as a brown viscous substance.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.02 (brs, 1H), 6.88 (brs, 1H), 3.91-3.62 (m, 3H), 3.51-1. 97 (m, 12H)

Synthesis Example 6: 2- (4-Bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5-{2- (methoxyimino) propyl} cyclopenta-2-enone (Compound No. 6-076) Production It was produced from 2- (4-bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopenta-2-enone in the same manner as in Synthesis Example 3.
Melting point; 150-153 ° C

Synthesis Example 7: 2- (4'-chloro-3-methoxy-5-methyl- [1,1'-biphenyl] -4-yl) -3-hydroxy-5-{2- (methoxyimino) propyl} cyclopenta Production of -2-enone (Compound No. 6-077) 2- (4-Bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5-{2- (methoxyimino) propyl} cyclopenta-2- In a mixed solution of 1.1 g of enone, 540 mg of 4-chlorophenylboronic acid, 8 ml of 1,4-dioxane and 2.5 ml of water, 2.2 g of tripotassium phosphate, [1,1'-bis (diphenylphosphino) ferrocene] 237 mg of palladium (II) dichloride dichloromethane adduct was added sequentially. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred at 100 ° C. for 2 hours. After completion of the reaction, a 1 mol / L hydrochloric acid aqueous solution was added to the reaction mixture to adjust the pH to 3, and the mixture was extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 8: 1 to 1: 1) to obtain 1.1 g of the target product as an orange viscous substance. rice field.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ11.36 (brs, 1H), 7.59-7.34 (m, 4H), 7.09-6.87 (m, 2H), 4. 00-3.78 (m, 6H), 3.54-3.32 (m, 1H), 3.09-2.50 and 2.38-1.81 (m, 10H)

Synthesis Example 8: 2- (4'-chloro-3-methoxy-5-methyl- [1,1'-biphenyl] -4-yl) -4- {2- (methoxyimino) propyl} -3-oxocyclo Production of Penta-1-ene-1-ylmorpholin-4-carboxylate (Compound No. 6-078) 2- (4'-Chloro-3-methoxy-5-methyl- [1,1'-biphenyl]- 4-Il) -3-hydroxy-5-{2- (methoxyimino) propyl} cyclopenta-2-enoone 70 mg and N, N-dimethylformamide 3 ml in a mixed solution, potassium carbonate 35 mg, then 4-morpholinylcarbonyl chloride. 31 mg was added sequentially, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 5 ml of water was added to the reaction solution, and the mixture was extracted with 5 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was expressed as n-hexane-ethyl acetate (3: 1-1: 1).
Purification by medium pressure preparative liquid chromatography eluting with 1 gradient) gave 77 mg of the target product as a colorless oil.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.58-7.34 (m, 4H), 7.03 (s, 1H), 6.90-6.86 (m, 1H), 3. 92-3.22 (m, 15H), 3.09-2.68 (m, 3H), 2.40-2.13 (m, 4H), 1.88 (s, 3H)

Synthesis Example 9: Production of 3-hydroxy-2- (2-methoxy-4,6-dimethylphenyl) -5- {2- (methoxyimino) propyl} cyclopenta-2-enone (Compound No. 6-037) 2 -(4-Bromo-2-methoxy-6-methylphenyl) -3-hydroxy-5-{2- (methoxyimino) propyl} cyclopenta-2-enoone 1 g and trimethylboroxin 326 mg and 1,4-dioxane 25 ml To the mixed solution, 1.1 g of potassium carbonate and 424 mg of [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred at 90 ° C. for 3 hours. After completion of the reaction, a 1 mol / L hydrochloric acid aqueous solution was added to the reaction mixture to adjust the pH to 3, and the mixture was extracted with 25 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1) to obtain 496 mg of the target product as an orange viscous substance.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ11.00 (brs, 1H), 6.78-6.53 (m, 2H), 4.05-3.70 (m, 6H), 3. 50-3.28 (m, 1H), 3.00-2.55 (m, 3H), 2.40-1.80 (m, 10H).

Synthesis Example 10: 3- (benzyloxy) -2-mesityl-5-{2- (methoxyimino) propyl} cyclopenta-2-enonone and 3- (benzyloxy) -2-mesityl-4- {2- (methoxy) Preparation of Mixture of Imino) propyl} Cyclopenta-2-enone (Compound No. 1-009) 3-Hydroxy-2-mesityl-5- {2- (methoxyimino) propyl} cyclopenta-2-enoone 500 mg and acetone 6 ml To the mixed solution, 458 mg of potassium carbonate and then 341 mg of benzyl bromide were sequentially added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, and the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 5: 1 to 1: 1) to obtain 680 mg of the desired product as a colorless oil.
^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.28-7.03 (m, 5H), 6.92-6.80 (m, 2H), 4.97-4.92 and 4.73 -4.68 (m, 2H), 3.86-3.77 (m, 3H), 3.31-1.80 (m, 17H).
The obtained target product was a mixture of 1-009a-1, 1-009a-2, 1-009b-1 and 1-009b-2, and the mixing ratio was 16: 3: 8: 1. The mixing ratio was determined by qualitative analysis by high performance liquid chromatography [mobile phase; {(acetonitrile: water = 4: 1) + volume ratio 1% acetic acid}, measurement wavelength; 254 nm]. The structures of 1-009a-1, 1-009a-2, 1-009b-1 and 1-009b-2 are as follows.

Synthesis Example 11: 3- (benzyloxy) -2-mesityl-5- {2- (methoxyimino) propyl} -5-methylcyclopenta-2-enoone (Compound No. 11-001) and 3- (benzyloxy) ) -2-Mesityl-4- {2- (methoxyimino) propyl} -5-Methylcyclopenta-2-enoone (Compound No. 12-001) 3- (benzyloxy) -2-mesityl-5- A mixture of {2- (methoxyimino) propyl} cyclopenta-2-enone and 3- (benzyloxy) -2-mesityl-4- {2- (methoxyimino) propyl} cyclopenta-2-enone (Compound No. 1- 009) A mixed solution of 611 mg and 7 ml of tetrahydrofuran is cooled to −78 ° C. under a nitrogen atmosphere, and then lithium diisopropylamide (a mixed solution of about 1.5 mol / L n-hexane and tetrahydrofuran, manufactured by Kanto Chemical Co., Ltd.) is added to the mixed solution. ) 1.7 ml was added dropwise. After completion of the dropping, the reaction mixture was stirred at the same temperature for 30 minutes. After completion of stirring, 244 mg of iodomethane was added to the reaction mixture. After completion of the addition, the reaction mixture was heated to room temperature and stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was added to 30 ml of ice water and extracted with 20 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by high performance liquid chromatography eluting with acetonitrile-water [4: 1 (volume ratio)] to obtain Compound No. Using 173 mg of 11-001 as a colorless oil, Compound No. Each of 12-001 86 mg was obtained as a colorless oil.
Compound No. 11-001: ^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.39-7.12 (m, 5H), 6.86 (brs, 2H), 4.96 (s, 2H), 3. 81 (s, 3H), 3.27-3.13 (m, 1H), 2.61-2.22 (m, 6H), 2.06 (brs, 6H), 1.87-1.77 ( m, 3H), 1.26 (s, 3H).
Compound No. 12-001: ^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.37-7.25 (m, 3H), 7.14-7.04 (m, 2H), 6.86 (brs, 2H) ), 4.71 (s, 2H), 3.83 (s, 3H), 2.88-2.77 (m, 2H), 2.47-2.23 (m, 5H), 2.15- 2.02 (m, 6H), 1.88 (s, 3H), 1.37-1.22 (m, 3H).

Examples of synthesis of a production intermediate for producing the compound of the present invention will be specifically described below as Reaction Example 1 and Reaction Example 2, but the production intermediate of the present invention is not limited to these.

Reaction Example 1: Production of 2- (2,6-dimethoxy-4-methylphenyl) cyclopenta-4-ene-1,3-dione Step 1: (2,6-dimethoxy-4-methylphenyl) (furan-2) -Il) Preparation of methanol A mixed solution of 0.69 g of furan and 10 ml of tetrahydrofuran was cooled to −10 ° C. under a nitrogen atmosphere. N-Butyllithium (1.6M tetrahydrofuran solution) in the mixed solution
6.9 ml was added, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. A mixed solution of 2.0 g of 2,6-dimethoxy-4-methylbenzaldehyde and 10 ml of tetrahydrofuran was added to the reaction solution at −10 ° C., the temperature of the reaction solution was raised to room temperature, and the mixture was stirred for 12 hours. After completion of the reaction, the reaction solution was poured into ice water and extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 1.89 g of the target product as a yellowish white solid.
Melting point; 75-85 ° C
Step 2: Preparation of 2- (2,6-dimethoxy-4-methylphenyl) cyclopenta-4-ene-1,3-dione (2,6-dimethoxy-4-methylphenyl) (furan-2-yl) methanol A mixed solution of 100 mg and 1 ml of water was irradiated with microwaves (200 W) using a microwave synthesizer and stirred at 200 ° C. for 30 minutes. After completion of the reaction, the reaction solution was extracted with 3 ml of ethyl acetate, the obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 5 ml of dichloromethane and 0.13 g of pyridinium chlorochromate were sequentially added to the obtained residue, and the mixture was stirred at room temperature for 2 hours after the addition was completed. After completion of the reaction, 5 ml of isopropyl alcohol was added to the reaction solution, and then the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (2: 1) to obtain 20 mg of the target product as a yellow solid.
Melting point: 122-126 ° C

Reaction Example 2: Production of 2- (2-Methoxy-4,6-dimethylphenyl) cyclopenta-4-ene-1,3-dione Journal of the American Chemical Society 2000, Vol. 122, pp. 5043. 2- (2-Methoxy-4,6-dimethylphenyl) cyclopenta-by the same method as in Steps 1 to 4 of Synthesis Example 5, using 10.0 g of 2-methoxy-4,6-dimethylaniline as a raw material. 0.2 g of 4-ene-1,3-dione was obtained as a yellow solid.
Melting point; 123-125 ° C

The compound of the present invention can be synthesized according to the above-mentioned production example. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 11 are shown in Tables 5 to 20, but the present invention is not limited to these. In the table, the description of Me represents a methyl group, the description of Et below represents an ethyl group, n-Pr and Pr-n represent a normal propyl group, and i-Pr and Pr-i represent an isopropyl group. , C-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n normal butyl groups, s-Bu and Bu-s are secondary butyl groups, and i-Bu and Bu-i are isobutyl groups. , T-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, and c-Pen and Pen-c are cyclopentyl groups. , N-Hex and Hex-n represent a normal hexyl group, c-Hex and Hex-c represent a cyclohexyl group, Hept represents a heptyl group, Oct represents an octyl group, Ph represents a phenyl group, and D1-1a. , D1-2c, D1-5d, D1-5e, D1-6d, D1-7a, D1-7b, D1-8b, D1-10d, D1-11a, D1-22a, D1-32a, D1-32b, D1 -33b, D1-34a, D1-37a, D1-81a, D1-84a, D1-103a, D1-103b, D1-103c, D1-103d, D1-103e, D1-103f, D1-103g, D1-103h , D1-103i, D1-103j, D1-103k, D1-103l, D1-103m, D1-108b, D1-108c, D1-108d, D1-108e represent the following structures, and D1-108e. 5d, D1-5e, D1-6d, D1
The numbers in the structural formulas of -7b, D1-10d, D1-32b, and D1-33b ^{represent the replacement positions of X 1} , and the numbers in the structural formula of D1-108b are the replacement positions of ^{Z 3.} The number written in ^{the structural formula of D1-108c represents the replacement position of Z 1} , and the number written in the structural formula of D1-108d represents the replacement position of Z ² .
Further, in the table, the description of "mp" means "melting point", the description of "* 1" means "resin-like", and the description of "decomp." Means decomposition.

なお、本発明化合物Ｎｏ．１−００９は化合物Ｎｏ．１−００９ａ−１，１−００９ａ−２，１−００９ｂ−１及び１−００９ｂ−２の混合物であり、１−００９ａ−１と１−００９ａ−２及び１−００９ｂ−１と１−００９ｂ−２はそれぞれオキシム部の幾何異性体を表す。 [Table 5]

In addition, the compound No. 1 of the present invention. 1-009 is compound No. It is a mixture of 1-009a-1, 1-009a-2, 1-009b-1 and 1-009b-2, 1-009a-1 and 1-009a-2 and 1-009b-1 and 1-009b-. 2 represents the geometric isomer of the oxime portion, respectively.

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

^{Table 21 shows 1 1} H-NMR data of the compounds of the present invention for which the melting point is not described.
Incidentally, proton nuclear magnetic resonance chemical shift values, using _Me 4 Si (tetramethylsilane) as the reference substance, in deuterochloroform solvent, was measured at 300 MHz. The symbols in Table 21 have the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, m: multiplet. In addition, for signals that can be analyzed in the presence of two or more structural isomers, each chemical shift value is marked with "and".

[Table 21]

Test Examples Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples, but the present invention is not limited to these.
[Test Example 1] Test of herbicidal effect by pretreatment for weed growth under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. After seeds of Nobie, Scirpus juncoides and Pontederia vaginalis were mixedly sown in the above cups, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dosage and treated on the surface of the water. The cups were placed in a greenhouse at 25 to 30 ° C. to grow plants, and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the following criteria. The results are shown in Table 22.
Judgment Criteria 5 ... Weed killing rate 90% or more (almost complete death)
4… Weeding rate 70% or more and less than 90% 3… Weeding rate 40% or more and less than 70% 2… Weeding rate 20% or more and less than 40% 1… Weeding rate 5% or more and less than 20% 0… Weeding rate 5% or less (almost effective) none)

[Test Example 2] Test of herbicidal effect by weed growing season treatment under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. Seeds of Nobie, Scirpus juncoides and Pontederia vaginalis were mixedly sown in the above cups and placed in a greenhouse at 25 to 30 ° C. to grow plants. When Nobie, Scirpus juncoides and Pontederia vaginalis reached the 1st or 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 23.

[Test Example 3] Test of herbicidal effect by foliage treatment After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed, and the condition was set to a water depth of 0.1 to 0.5 cm. Seeds of barnyard grass, leptochloa zebra, cyperus difformis and rice were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 24.

[Test Example 4] Test of herbicidal effect by soil treatment Put sterilized white goosefoot in a plastic box with a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Seeds of grass, amaranthus retroflexus, white goosefoot, hakobe, yaemgra, oat, oat, corn, soybean, rice, wheat, beet and rapeseed were sown in spots and covered with soil of about 1.5 cm. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the soil surface was uniformly treated with a small spray. Plants were grown by placing a plastic box in a greenhouse at 25 to 30 ° C., and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 25.

[Test Example 5] Test of herbicidal effect by foliage treatment Put sterilized white goosefoot in a plastic box with a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Seeds of grass, amaranthus retroflexus, white goosefoot, crabgrass, yaemgra, oat, oat, corn, soybean, rice, wheat, beet and rapeseed are sown in spots, covered with soil about 1.5 cm, and then planted in a greenhouse at 25 to 30 ° C. Was cultivated. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 26.

The symbols in Tables 22 to 26 have the following meanings.
A: Nobie, B: Hotarui, C: Konagi, D: Azegaya, E: Kogomegayatsuri, F: Mehishiba, G: Enokorogusa, H: Inubier, I: Karasumugi, J: Blackgrass, K: Italian ryegrass, L: Seiyounukabo , M: Ichibi, N: Amaranthus retroflexa, O: White goosefoot, P: Hakobe, Q: Yaemgra, R: Oinunofuguri, a: Transplanted rice, b: Directly sown rice, c: Corn, d: Soybean, e: Wheat, f: Beat , G: Rapeseed Rice The amount of treated drug (g / ha) means that the concentration was adjusted so that only the number of grams (g) of the stated value was processed when converted per 1 hectare (1 ha). ..

[Table 22]

[Table 23]

[Table 24]

[Table 25]

[Table 26]

The ketone or oxime compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Claims (4)

Equation (1):

[In the formula, B represents the ring represented by either B-1-a or B-2-a.

Q represents an oxygen atom
A represents a hydrogen atom, C _{1 to} C ₆ alkyl or -C (O) R ² .
R ² represents C _{1 to} C ₈ alkyl and represents
R ⁶ is C _{1 to} C ₆ alkyl, optionally substituted with ^{R 15} _{(C 1 to} C ₆ ) alkyl, C.
Represents _{3 to C 8} cycloalkyl, C _{2 to} C ₆ alkenyl, -C (= NOR ¹⁶ ) R ¹⁷ , phenyl, phenyl or D1-32 substituted with ^{(Z 1} ) _q1.
R ^8a represents a hydrogen atom, C _{1 to} C ₆ alkyl, -C (O) OR ^16a or -C (O) R ^17a .
R ^9a represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ^8b and R ^9b represent a hydrogen atom and represent a hydrogen atom.
R ¹⁰ , R ¹¹ and R ¹² represent a hydrogen atom.
R ¹⁵ represents a halogen atom, C _{3 to} C ₈ cycloalkyl, -OR ¹⁶ or phenyl.
R ¹⁶ , R ^16a , R ¹⁷ and R ^17a each independently _{represent C 1 to} C ₆ alkyl.
Z ^a , Z ^c and ^Ze were independently substituted with hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl and R ⁴⁵ , respectively. (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, -OR ⁴¹ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-7, D1-11, D1-22, D1-32 or D1 Represents -37
Z ¹ represents a halogen atom
Z ³ represents a halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy or C _{1 to} C ₆ alkyl thio.
R ⁴¹ _represents C 1 -C ₆ ^alkyl, optionally substituted with ^{R 45} _(C 1 ~C ₆₎ alkyl, phenyl, a D1-32 or D1-34,
R ⁴⁵ represents a halogen atom, phenyl or D1-34.
D1-7, D1-11, D1-22, D1-32, D1-34 or D1-37 each represent a ring represented by the following structure.

X ¹ represents halo (C _{1 to} C ₆ ) alkyl,
g2, g3 and p represent 0 and
m, q1 and q3 represent integers of 1.
g4 and n independently represent an integer of 0 or 1, respectively. ] Represented by a ketone compound or a salt thereof. B represents B-1-a and represents
Z ^a represents a halogen _atom, C 1 -C ₆ alkyl or _C 1 -C ₆ alkoxy,
Z ^c is optionally substituted with halogen atoms, C _{1 to} C ₆ alkyl, C _{3 to} C ₈ cycloalkyl, C _{2 to} C ₆ alkenyl, R ⁴⁵ _{(C 2 to} C ₆ ) alkenyl, C ₂ to C. ₆ Represents alkynyl, -OR ⁴¹ , phenyl, phenyl ^{substituted with (Z 3} ) _q3 , D1-7, D1-11, D1-22, D1-32 or D1-37.
^Ze is the ketone compound according to claim 1 or a salt thereof, which represents a halogen atom or C _{1 to} C _{6 alkyl.} A pesticide containing one or more selected from the ketone compound according to claim 1 or claim 2 and a salt thereof as an active ingredient. A herbicide containing one or more selected from the ketone compound according to claim 1 or claim 2 and a salt thereof as an active ingredient.